Scholars@Duke
Andrew T. McPhail

Andrew T. McPhail

Professor Emeritus of Chemistry
Chemistry
Box 90346, Durham, NC 27708-0346
3236 French Family Science, Box 90347, Durham, NC 27708
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Selected Publications

A highly stereoselective approach to novel 2,2,4-trisubstituted pyrrolidines by halocylization: Key intermediates towards syntheses of nitrogen analogs of Noxafil®

Journal Article Tetrahedron Letters · October 20, 2003 A convenient synthesis of novel 2,2,4-trisubstituted pyrrolidines via stereoselective 5-exo iodocyclization of the 2,2-disubstituted olefins 8 and 9 is described. Single crystal X-ray analysis of the oxazolidinone 15 confirmed the relative stereochemistry ... Full text Cite

An unusual acetonide group migration

Journal Article Tetrahedron Letters · September 15, 2003 Treatment of (2S,3R)-2,3-O-isopropyliden-4-penten-1,2,3-triol mesylate with uracil, K2CO3 did not provide the product of S N2 displacement, but an interesting acetonide group migration product 8. The structure of 8 was secured by spectral analysis and sing ... Full text Cite

Synthesis and NK(1)/NK(2) binding activities of a series of diacyl-substituted 2-arylpiperazines.

Journal Article Bioorganic & medicinal chemistry letters · November 2002 The synthesis and binding affinity for hNK(1) and hNK(2) receptors of a series of diacyl substituted 2-aryl piperazines are described. SAR evaluation led to the racemic derivative 11g as an apparent dual inhibitor. Chiral chromatographic separation of 11g ... Full text Cite

Antitumor agents. Part 215: antitubulin effects of cytotoxic B-ring modified allocolchicinoids.

Journal Article Bioorganic & medicinal chemistry letters · October 2002 N-Acetylcolchinol methyl ether 1 served as the starting material to prepare the chloroacetamide (3) and epoxide (5) analogues. Both 3 and 5 were potent inhibitors of tubulin polymerization in vitro. Compound 3 was also 4-fold more cytotoxic than colchicine ... Full text Cite

The asymmetric synthesis of (3R)-N-methyl-2-oxo-[1,4′-bipiperidine]-3-acetamide in quantity

Journal Article Tetrahedron Asymmetry · June 24, 2002 The asymmetric synthesis of the enantiomerically pure bipiperidine core fragment of a potent dual NK1/NK2 antagonist is described. The utilization of a diastereoselective Michael addition employing Evans' auxiliary as the key step allowed for the preparati ... Full text Cite

Application of ruthenium-induced macrocyclization for the construction of macrocyclic depsipeptides.

Journal Article The Journal of organic chemistry · May 2002 The synthesis of a biaryl ether containing macrocyclic depsipeptide 1 was achieved in 6% overall yield. The desired macrocycle was constructed by cyclization of a phenol into eta(6)-ruthenium complex. The ruthenium metal was subsequently photolytically dep ... Full text Cite

Desmosdumotin C, a novel cytotoxic principle from Desmos dumosus

Journal Article Tetrahedron Letters · February 18, 2002 The structure of desmosdumotin C (1), a novel compound isolated from the roots of Desmos dumosus, has been established from spectral data and X-ray crystallographic analysis. Significant and selective in vitro cytotoxicity of 1 was found against bone (HOS) ... Full text Cite

A novel protonated boranoamino acid amide derivative, (CH3)3N · BH2C(OH)=N+HC2H5Cl-: A synthetic and structural investigation

Journal Article Inorganic Chemistry Communications · July 4, 2001 The reaction between Me3N · BH2CONHC2H5 (1) and anhydrous HCl gas in diethyl ether resulted in the formation of an unprecedented salt, Me3N · BH2C(OH)=N+HC2H5Cl- (2), whose crystal structure unambiguously shows that the amide hydrogen atom is oriented in t ... Full text Cite

N-methylated 5-alkenyloxazolium salt transformations.

Journal Article Organic letters · July 2001 [reaction: see text] In the course of natural product synthetic studies, 5-(4-pentenyl)oxazole and 5-(5-hexenyl)oxazole were N-methylated. The initial N-methylated 5-alkenyloxazolium salt adducts were found to be only intermediates and were ultimately tran ... Full text Cite

Total synthesis of himandravine.

Journal Article Organic letters · May 2001 [reaction: see text] The first total synthesis of (+)-himandravine (1) is described, starting from (2S,6S)-cis-2-formyl-6-methyl-N-Boc-piperidine (8) in 11 linear steps and 17% overall yield. The key step involves a highly diastereoselective intramolecular ... Full text Cite

Anti-AIDS agents. 42. Synthesis and anti-HIV activity of disubstituted (3'R,4'R)-3',4'-di-O-(S)-camphanoyl-(+)-cis-khellactone analogues.

Journal Article Journal of medicinal chemistry · March 2001 A series of disubstituted 3',4'-di-O-(S)-camphanoyl-(+)-cis-khellactone (DCK) analogues (1-10) were synthesized and evaluated for inhibition of HIV-1 replication in H9 lymphocytes. 5-Methoxy-4-methyl DCK (8) was the most promising compound with an EC(50) v ... Full text Cite

Microbial hydroxylation and reduction of the diterpene psiadin.

Journal Article Zeitschrift fur Naturforschung. C, Journal of biosciences · March 2001 Microbial bioconversion studies conducted on the diterpene psiadin have revealed that it was metabolized by Aspergillus niger (NRRL 2295) to give 2alpha-hydroxydeoxopsiadin, Cunninghamella blakesleeana (ATCC 8688a) to give 11beta-hydroxypsiadin, and Cylind ... Full text Cite

Further Alkaloids from Haplophyllum tuberculatum

Journal Article Phytochemistry · 2001 Cite

cis-parthenolid-9-one from Anvillea garcinii.

Journal Article Journal of natural products · November 2000 The cis-isomer (2) of the previously isolated parthenolid-9-one (1) was isolated from Anvillea garcinii and the structures and relative stereochemistries of both were determined from NMR data in combination with single-crystal X-ray analysis. In vitro cyto ... Full text Cite

An asymmetric synthesis of the novel H3 agonist (+)-(3R,4R)-3-(4-imidazolyl)-4-methylpyrrolidine dihydrochloride (Sch 50971)

Journal Article Tetrahedron Asymmetry · October 6, 2000 A short, high yielding, enantioselective synthesis of the novel H3 agonist Sch 50971 1 is described. The key enantiodifferentiating step is the 1,4-addition of a chiral N-propionyloxazolidinone to a nitroolefin. Copyright (C) 2000 Elsevier Science Ltd. ... Full text Cite

A highly stereoselective approach to novel 2,2,4-trisubstituted pyrrolidines by halocylization: Key intermediates towards syntheses of nitrogen analogs of Noxafil®

Journal Article Tetrahedron Letters · October 20, 2003 A convenient synthesis of novel 2,2,4-trisubstituted pyrrolidines via stereoselective 5-exo iodocyclization of the 2,2-disubstituted olefins 8 and 9 is described. Single crystal X-ray analysis of the oxazolidinone 15 confirmed the relative stereochemistry ... Full text Cite

An unusual acetonide group migration

Journal Article Tetrahedron Letters · September 15, 2003 Treatment of (2S,3R)-2,3-O-isopropyliden-4-penten-1,2,3-triol mesylate with uracil, K2CO3 did not provide the product of S N2 displacement, but an interesting acetonide group migration product 8. The structure of 8 was secured by spectral analysis and sing ... Full text Cite

Synthesis and NK(1)/NK(2) binding activities of a series of diacyl-substituted 2-arylpiperazines.

Journal Article Bioorganic & medicinal chemistry letters · November 2002 The synthesis and binding affinity for hNK(1) and hNK(2) receptors of a series of diacyl substituted 2-aryl piperazines are described. SAR evaluation led to the racemic derivative 11g as an apparent dual inhibitor. Chiral chromatographic separation of 11g ... Full text Cite

Antitumor agents. Part 215: antitubulin effects of cytotoxic B-ring modified allocolchicinoids.

Journal Article Bioorganic & medicinal chemistry letters · October 2002 N-Acetylcolchinol methyl ether 1 served as the starting material to prepare the chloroacetamide (3) and epoxide (5) analogues. Both 3 and 5 were potent inhibitors of tubulin polymerization in vitro. Compound 3 was also 4-fold more cytotoxic than colchicine ... Full text Cite

The asymmetric synthesis of (3R)-N-methyl-2-oxo-[1,4′-bipiperidine]-3-acetamide in quantity

Journal Article Tetrahedron Asymmetry · June 24, 2002 The asymmetric synthesis of the enantiomerically pure bipiperidine core fragment of a potent dual NK1/NK2 antagonist is described. The utilization of a diastereoselective Michael addition employing Evans' auxiliary as the key step allowed for the preparati ... Full text Cite

Application of ruthenium-induced macrocyclization for the construction of macrocyclic depsipeptides.

Journal Article The Journal of organic chemistry · May 2002 The synthesis of a biaryl ether containing macrocyclic depsipeptide 1 was achieved in 6% overall yield. The desired macrocycle was constructed by cyclization of a phenol into eta(6)-ruthenium complex. The ruthenium metal was subsequently photolytically dep ... Full text Cite

Desmosdumotin C, a novel cytotoxic principle from Desmos dumosus

Journal Article Tetrahedron Letters · February 18, 2002 The structure of desmosdumotin C (1), a novel compound isolated from the roots of Desmos dumosus, has been established from spectral data and X-ray crystallographic analysis. Significant and selective in vitro cytotoxicity of 1 was found against bone (HOS) ... Full text Cite

A novel protonated boranoamino acid amide derivative, (CH3)3N · BH2C(OH)=N+HC2H5Cl-: A synthetic and structural investigation

Journal Article Inorganic Chemistry Communications · July 4, 2001 The reaction between Me3N · BH2CONHC2H5 (1) and anhydrous HCl gas in diethyl ether resulted in the formation of an unprecedented salt, Me3N · BH2C(OH)=N+HC2H5Cl- (2), whose crystal structure unambiguously shows that the amide hydrogen atom is oriented in t ... Full text Cite

N-methylated 5-alkenyloxazolium salt transformations.

Journal Article Organic letters · July 2001 [reaction: see text] In the course of natural product synthetic studies, 5-(4-pentenyl)oxazole and 5-(5-hexenyl)oxazole were N-methylated. The initial N-methylated 5-alkenyloxazolium salt adducts were found to be only intermediates and were ultimately tran ... Full text Cite

Total synthesis of himandravine.

Journal Article Organic letters · May 2001 [reaction: see text] The first total synthesis of (+)-himandravine (1) is described, starting from (2S,6S)-cis-2-formyl-6-methyl-N-Boc-piperidine (8) in 11 linear steps and 17% overall yield. The key step involves a highly diastereoselective intramolecular ... Full text Cite

Anti-AIDS agents. 42. Synthesis and anti-HIV activity of disubstituted (3'R,4'R)-3',4'-di-O-(S)-camphanoyl-(+)-cis-khellactone analogues.

Journal Article Journal of medicinal chemistry · March 2001 A series of disubstituted 3',4'-di-O-(S)-camphanoyl-(+)-cis-khellactone (DCK) analogues (1-10) were synthesized and evaluated for inhibition of HIV-1 replication in H9 lymphocytes. 5-Methoxy-4-methyl DCK (8) was the most promising compound with an EC(50) v ... Full text Cite

Microbial hydroxylation and reduction of the diterpene psiadin.

Journal Article Zeitschrift fur Naturforschung. C, Journal of biosciences · March 2001 Microbial bioconversion studies conducted on the diterpene psiadin have revealed that it was metabolized by Aspergillus niger (NRRL 2295) to give 2alpha-hydroxydeoxopsiadin, Cunninghamella blakesleeana (ATCC 8688a) to give 11beta-hydroxypsiadin, and Cylind ... Full text Cite

Further Alkaloids from Haplophyllum tuberculatum

Journal Article Phytochemistry · 2001 Cite

cis-parthenolid-9-one from Anvillea garcinii.

Journal Article Journal of natural products · November 2000 The cis-isomer (2) of the previously isolated parthenolid-9-one (1) was isolated from Anvillea garcinii and the structures and relative stereochemistries of both were determined from NMR data in combination with single-crystal X-ray analysis. In vitro cyto ... Full text Cite

An asymmetric synthesis of the novel H3 agonist (+)-(3R,4R)-3-(4-imidazolyl)-4-methylpyrrolidine dihydrochloride (Sch 50971)

Journal Article Tetrahedron Asymmetry · October 6, 2000 A short, high yielding, enantioselective synthesis of the novel H3 agonist Sch 50971 1 is described. The key enantiodifferentiating step is the 1,4-addition of a chiral N-propionyloxazolidinone to a nitroolefin. Copyright (C) 2000 Elsevier Science Ltd. ... Full text Cite

IMDA/aldol strategy for transforming carbohydrates into functionalized trans-decalins.

Journal Article Chirality · June 2000 L-Rhamnal is readily converted into an allyl 2, 3-unsaturated-C-glycopyranoside. The (S) configuration of the alphaL-anomer defines the stereochemical outcome of the future IMDA reaction, leading to the absolute stereochemistry for the trans-decalin moiety ... Full text Cite

A facile Diels-Alder route to dihydronaphthofuranones

Journal Article Tetrahedron Letters · May 29, 2000 An efficient, multigram-scale synthesis of dihydronaphthofuranone 1 using a novel aryl intramolecular Diels-Alder reaction of propargyl trans- cinnamate 8 is described. Catalytic reduction of 1 gave the cis-fused tetrahydronaphthofuranone derivative 2. (C) ... Full text Cite

A novel microbial metabolite, activator of low density lipoprotein receptor promoter

Journal Article Tetrahedron Letters · February 26, 2000 The organic extract of the fermentation broth of a Micromonospora microorganism was found to contain SCH 351448 (1), the monosodium salt of a macrocyclic dilactone containing two identical diacids. The structure and relative stereochemistry were establishe ... Full text Cite

Conformational considerations in the design of dual antagonists of platelet-activating factor (PAF) and histamine.

Journal Article Bioorganic & medicinal chemistry · July 1999 Following the discovery of the first dual antagonist of platelet-activating factor (PAF) and histamine, 1-acetyl-4-(8-chloro-5,6-dihydro-11H-benzo[5,6]cyclohepta[1,2-b]pyridin- 11-ylidene)piperidine, Sch 37370, 1, a related series of structures, exemplifie ... Full text Cite

Total Synthesis of (+)-Himbacine and (+)-Himbeline.

Journal Article The Journal of organic chemistry · March 1999 Himbacine (1), a complex piperidine alkaloid isolated from the bark of Australian magnolias, is a promising lead in Alzheimer's disease research due to its potent muscarinic receptor antagonist property. We have described here a highly efficient synthetic ... Full text Cite

Mycoepoxydiene represents a novel class of fungal metabolites

Journal Article Tetrahedron Letters · February 19, 1999 A novel epoxycyclooctadiene-δ-lactone, mycoepoxydiene, was isolated from a fungal culture (OS-F66617). Its structure and relative stereochemistry were established using spectroscopic studies, including single-crystal X-ray diffraction analysis. ... Full text Cite

Antitumor agents. 190. Absolute stereochemistry of the cytotoxic germacranolides, tomenphantins A and B, from Elephantopus tomentosus.

Journal Article Journal of natural products · February 1999 The structures and absolute stereochemistries of tomenphantins A (1) and B (2), cytotoxic germacranolides isolated from Elephantopus tomentosus, are reported herein. 1H and 13C NMR spectroscopic data, chemical transformation, and single-crystal X-ray analy ... Full text Cite

New products from the reactions of artemisinin with ammonia and amines

Journal Article Journal of natural products · January 1999 Reaction of artemisinin (1) with ammonia, methylamine, dimethylamine, and allylamine afforded five unexpected products 2-6, in addition to the previously reported compounds 7-12. The identities of the new compounds were established from their spectral data ... Full text Cite

Antitumor agents. 192. Antitubulin effect and cytotoxicity of C(7)-oxygenated allocolchicinoids

Journal Article Collection of Czechoslovak Chemical Communications · January 1, 1999 Two allocolchicinoids 6 and 8, prepared from colchicine, together with allo compounds 9-11, made from 6 by reduction and regiodemethylation, were evaluated for antitubulin and antitumor activities. Structures of 6, 8, and 10 were confirmed by X-ray crystal ... Full text Cite

Synthesis of a trifluoromethylindolocarbazole, novel cyclic 27- and 36-membered N-benzyltri- and -tetraindoles, and an N-benzyltetraindolyltrimethane

Journal Article Monatshefte fur Chemie · January 1, 1999 5,11-Dihydro-5,11-dibenzyl-6-trifluoromethylindolo[3,2-b]carbazole (6) and the cyclic N-benzylindole trimer 4 were synthesized from both N-benzylindole-3-methanol (1) and N,N'-dibenzyl-3,3'-diindolylmethane (2) by treatment with trifluoroacetic anhydride. ... Full text Cite

Synthesis of a C11 spirocyclopropyl derivative of 8-chloro-6,11- dihydro-5h-benzo[5,6]cyclohepta[1,2b]pyridine

Journal Article Tetrahedron Letters · October 15, 1998 The carbanion derived from 8,11-dichloro-6,11-dihydro-5H- benzo[5,6]cyclohepta[1,2-b] pyridine (3) reacts with methyl acrylate to form the C11 spirocyclopropane carboxylic acid methyl ester 6. Compound 6 was converted in five steps to the N-methyl 2'-ethyl ... Full text Cite

Synthesis of a C11 spiropiperidino derivative of 8-chloro-6,11- dihydro 5H-benzo[5,6]cyclohepta[1,2-b]pyridine

Journal Article Tetrahedron Letters · October 15, 1998 A method using N-tosyl aziridine for the synthesis of a spiropiperidine 2 (R=H) is described. Cleavage of the N-tosyl group of the intermediate 8 to form the spiropiperidinone 9 was found to proceed in high yield with conc. sulfuric acid. Acylated derivati ... Full text Cite

Beta-lactams derived from the reaction of phenanthridines and 11H- dibenzo[b,e]azepin-11-one with phenyivaleryl chloride. Synthesis of fused analogs of the cholesterol absorption inhibitor Sch 48461

Journal Article Tetrahedron Letters · October 8, 1998 Phenanthridines 4 and the 11H-dibenzo[b,e]azepin-11-one 17 were used as the imine components in the ketene-imine β-lactam synthesis to provide the fused tetracyclic β-lactams 7, 8 and 18. ... Full text Cite

Preparation and evaluation of a cyclic acyl nitrone as a synthon for stereospecific α-amino acid synthesis

Journal Article Tetrahedron Letters · September 17, 1998 The preparation and characterization of cyclic optically active (5R)- 3,4,5,6-tetrahydro-5-phenyl-2H-1,4-oxazin-2-one-N-oxide (2) is described. This nitrone, which is viewed as a template for the synthesis of γ- oxygenated α-amino acids, reacts with alkene ... Full text Cite

Preparation and X-ray crystal structure study of a polypyridyl ruthenium(II) complex containing a dehydrodithizone ligand

Journal Article Polyhedron · August 31, 1998 Coordination of 2,3-diphenyltetrazolium-5-thiolate (tet) to an Ru(trpy)(bpy)(OH2)2 (trpy=2,2′:6′,2″-terpyridine; bpy=2,2′-bipyridine) centre resulted in the formation of [Ru(trpy)(bpy) (tet)](ClO4)2. Single-crystal X-ray analysis revealed that the tet liga ... Full text Cite

In vitro metabolism of 10-(3-chlorophenyl)-6,8,9,10-tetrahydrobenzo[b][1,8]naphthyridin-5(7H)- one, a topical antipsoriatic agent. Use of precision-cut rat, dog, monkey and human liver slices, and chemical synthesis of metabolites.

Journal Article Biopharmaceutics & drug disposition · July 1998 The metabolism of SCH 40120, which is the clinically effective antipsoriatic drug 10-(3-chlorophenyl)-6,8,9,10-tetrahydrobenzol[b][1,8]naphthyrid in-5(7H)-one, was determined in vitro. Rat, dog, cynomolgus monkey, and human liver slices hydroxylated the al ... Full text Cite

Antitumor Agents. 183. Syntheses, Conformational Analyses, and Antitubulin Activity of Allothiocolchicinoids

Journal Article Journal of Organic Chemistry · June 12, 1998 7-O-Substituted analogues of allothiocochicine were synthesized and evaluated for their inhibitory effects on tubulin polymerization in vitro. Ketone 6, a key compound in this study, was derived from thiocolchicone 5 by ring contraction. The structure of 6 ... Full text Cite

Synthesis of isomeric 3-piperidinyl and 3-pyrrolidinyl benzo[5,6]cyclohepta[1,2-b]pyridines: sulfonamido derivatives as inhibitors of Ras prenylation.

Journal Article Bioorganic & medicinal chemistry · June 1998 Blocking farnesylation of oncogenic Ras proteins is a mechanism based therapeutic approach that is of current interest for the development of antitumor agents to treat ras associated tumors. As part of a SAR study on the lead farnesyl protein transferase ( ... Full text Cite

An unusual dienone-phenol rearrangement product formed during the synthesis of mometasone furoate (Sch 32088).

Journal Article Steroids · March 1998 The structure of an unusual dienone-phenol rearrangement product 4 obtained during the synthesis of mometasone furoate (Sch 32088) was assigned on the basis of NMR and x-ray crystallographic data. The mechanism of formation is discussed. ... Full text Cite

Synthesis of C3 heteroatom-substituted azetidinones that display potent cholesterol absorption inhibitory activity.

Journal Article Journal of medicinal chemistry · February 1998 The C3 phenylpropyl side chain of N-phenylazetidinones related to SCH 56524 was modified by replacing the hydroxymethylene with various isoelectronic or isosteric groups. Modifications at the 3' position led to less-active compounds; however, modifications ... Full text Cite

Revised Relative and Absolute Stereochemistry of (+)-Purpurin

Journal Article Journal of natural products · January 1998 The relative and absolute stereochemistries of (+)-purpurin (3), a flavanone natural product from Tephrosia, were determined to be 2S,7aR,10S,10aS by synthesis from semiglabrin in conjunction with X-ray crystallographic analysis. ... Full text Cite

Boron trifluoride-acetic anhydride catalysed rearrangement of dihydroarteannuin B

Journal Article Tetrahedron · November 3, 1997 The reaction of dihydroarteannuin B 2 with boron trifluoride-acetic anhydride furnished compound 3 as the major product whose structure has been established by chemical transformations, spectral data and finally confirmed by x-ray analysis. ... Full text Cite

Reversal of expected stereochemical outcome in the oppolzer reaction of a cyclic N-enoylsultam: Enantioselective synthesis and absolute configuration of antispermatogenic hexahydroindeno[1,2-c]pyridines

Journal Article Tetrahedron Letters · May 26, 1997 p-Tolylmagnesium bromide added with high enantioselectivity to a cyclic enoylsultam (4), but the diastereofacial selectivity (determined by X-ray crystallography of the product) was opposite that reported for acyclic enoylsultams. The reaction was used in ... Full text Cite

Antitumor agents. 172. Synthesis and biological evaluation of novel deacetamidothiocolchicin-7-ols and ester analogs as antitubulin agents.

Journal Article Journal of medicinal chemistry · March 1997 A series of novel 7-O-substituted deacetamidothiocolchicine derivatives has been synthesized and evaluated for their inhibitory activity against tubulin polymerization, the binding of [3H]-colchicine to tubulin, and the growth of human Burkitt lymphoma cel ... Full text Cite

Hypoestenone: A fusicoccane diterpene ketone from Hypoestes forskalei

Journal Article Phytochemistry · January 1, 1997 The aerial parts of Hypoestes forskalei yielded a new fusicoccane diterpene ketone, named hypoestenone. Its structural assignment was based on chemical derivatization and 1H and 13C NMR spectroscopic studies, mainly 2D NMR experiments, including long range ... Full text Cite

Intramolecular oxidative transformations of l,4-diaryl-2,3-dimethyl-2,3-epoxybutane with DDQ

Journal Article Chinese Chemical Letters · December 1, 1996 Treatment of 1,4-diaryl-2,3-dimethyl-2,3-epoxide of butane(l) with 2,3- dichloro-5. 6-dicyano-1. 4-benzoquinone(DDQ) in trifluoroacetic acid (TFA) furnishes a new benzofuran type lignan (2). The structure of (2) was established by MS, IR, UV and NMR spectr ... Cite

Preparation and characterization of a new artemisinin-derived dimer

Journal Article Journal of Natural Products · October 1, 1996 A new dimer (1) that is likely to be a reduction metabolite of arteether (2), the potent antimalarial agent, was prepared from deoxydihydroartemisinin (3). The identity of 1 was established from spectral data and was confirmed by X-ray crystallographic ana ... Full text Cite

(-)-SCH 57939: Synthesis and pharmacological properties of a potent, metabolically stable cholesterol absorption inhibitor

Journal Article Bioorganic and Medicinal Chemistry Letters · September 3, 1996 Previous SAR studies of C-3 side chain modified analogs of (-)-SCH 48461, as well as information concerning the metabolic stability this series, enabled us to design a cholesterol absorption inhibitor (i.e., (-) 2a, SCH 57939) with tenfold higher potency a ... Full text Cite

Stereoselective synthesis and biological activity of cis azetidinones as cholesterol absorption inhibitors

Journal Article Bioorganic and Medicinal Chemistry Letters · August 20, 1996 The C-3 sidechain of azetidinones related to SCH 48461 was modified by introducing a hydroxyl group at the 1' position. This led to the discovery of the cis azetidinone 2c, which had improved CAI activity. Compound 2c was prepared using a selective reducti ... Full text Cite

A cembranolide diterpene farnesyl protein transferase inhibitor from the marine soft coral Lobophytum cristagalli

Journal Article Bioorganic and Medicinal Chemistry Letters · April 9, 1996 A previously described cembranolide diterpene from Lobophytum cristagalli was identified as a potent (IC50 0.15 μM) inhibitor of farnesyl protein transferase (FPT). The compound showed selectivity for FPT as compared to the closely related enzyme geranylge ... Full text Cite

Five new modified 6,7-secolabdane diterpenoids from Cluytia richardiana

Journal Article Journal of Natural Products · March 1, 1996 The aerial parts of Cluytia richardiana yielded five new modified 6,7- secolabdane diterpene derivatives, saudinolide (4), dihydrosaudinolide (5), 5β-hydroxyrichardianidin 1 (6), and 5β-hydroxyrichardianidin 2 (7), and the 6,7-seco-6,11-cyclo-20-norlabdane ... Full text Cite

Synthesis and evaluation of pyrazolo[3,4-b]quinoline ribofuranosides and their derivatives as inhibitors of oncogenic Ras

Journal Article Bioorganic and Medicinal Chemistry Letters · January 23, 1996 A series of pyrazolo[3,4-b]quinoline ribofuranosides were prepared using the glycosylation methodology of Vorbruggen. Oxidative cleavage of the ribose moiety in 6 furnished the dialdehyde intermediate 36, which cyclizes upon reductive amination providing t ... Full text Cite

Reactions of phenylaluminium compounds with E(SiMe3)3 (E = P or As): X-ray crystal structures of Ph3Al · E(SiMe3)3 (E = P or As) and Ph2(CI)Al · P(SiMe3)3

Journal Article Polyhedron · January 1, 1996 The independent reactions of Ph3Al with E(SiMe3)3 (E = P or As) in 1:1 mole ratios afforded the adducts Ph3Al · E(SiMe3)3 [E = P (I) and As (II), respectively]. The attempted dehalosilylation reactions between Ph2AlCl and E(SiMe3)3 (E = P or As) in 1:1 mol ... Full text Cite

Structural determination of two isomers of betamethasone by NMR spectroscopy

Journal Article Magnetic Resonance in Chemistry · January 1, 1996 Two isomers of betamethasone 9α-fluoro-11β,17α,21-trihydroxy-16β-methylpregna-1,4- diene-3,20-dione (1), were isolated from the mother liquor of a manufacturing process and were characterized by NMR spectroscopy. They were identified as 8α-fluoro-11β,17α,2 ... Full text Cite

Preparation and characterization of arsine derivatives: X-ray crystal structures of As(SitBuMe2)3,As(SiMe3) 2(SiPh3), Et3Ga · As(SiMe3)2(SiPh3), and As(SePh)3

Journal Article Heteroatom Chemistry · January 1, 1996 As(SitBuMe2)3 (1) was prepared by the salt-elimination reaction between (Na/K3)3As and tBuMe2SiCl. Mixing LiAs(SiMe3)2 with Ph3SiCl (1:1) yielded As(SiMe3)2(SiPh3) (2) in a good crystalline yield. Reaction of 2 (1:1) with Et3Ga gave the expected Lewis acid ... Full text Cite

1,3 acyclic control in free radical reactions: Threo-selective additions

Journal Article Tetrahedron Letters · November 6, 1995 Oxazolidinone acrylamides undergo addition reactions with alkyl iodides and allyltributylstannane to give 1,3-substituted products with a threo preference in excess of 10:1. This threo preference is highest for reactions carried out in nonpolar solvents, a ... Full text Cite

An unusual rearrangement product formed during production of mometasone furoate (Sch 32088).

Journal Article Steroids · September 1995 The structure of an unusual rearrangement product obtained during the production of mometasone furoate (Sch 32088) was assigned on the basis of NMR and X-ray crystallography data. ... Full text Cite

Synthesis and properties of novel substituted 4,5,6,7-tetrahydroindenes and selected metal complexes

Journal Article Journal of Organometallic Chemistry · April 5, 1995 The synthesis of a complete series of substituted 4,5,6,7-tetrahydroindenes (4,5,6,7-tetrahydroindene, 1; 1-methyl-, 1,3-dimethyl- and 1,2,3-trimethyl-4,5,6,7-tetrahydroindene, 2-4) is reported. The synthesis of ferrocenes (bd8-11) from these substituted c ... Full text Cite

Isolation and x-ray crystal structures of {Li2[μ2-As(SiMe3)2][μ3-As(SiMe3)2](THF)}2and [(Me3Si)2AsLi(THF)2]2

Journal Article Journal of Coordination Chemistry · February 1, 1995 The lithium arsenides {Li2[p2-As(SiMe3)2] [p3-As(SiMe3)2](THF)}2 (I) (THF = tetrahydrofuran) and [(Me3Si)2AsLi(THF)2]2 (II) were isolated and their solid-state structures determined by X-ray methods. Compound I crystallizes in the monoclinic system, space ... Full text Cite

Structure and stereochemistry of taxuchin A, a new 11(15→1) abeo-taxane type diterpene from Taxus chinensis

Journal Article Journal of the Chemical Society, Chemical Communications · December 1, 1994 Taxuchin A, a new 11(15→1) abeo-taxane type diterpene has been isolated from the bark of Taxus chinensis and structurally characterised from spectral data and X-ray crystallographic analysis. ... Full text Cite

Anti-AIDS agents. 15. Synthesis and anti-HIV activity of dihydroseselins and related analogs.

Journal Article J Med Chem · November 11, 1994 Forty-two dihydroseselins based on the structure of suksdorfin (1) were synthesized in order to evaluate their anti-HIV activity. These synthetic derivatives include 3',4'-di-O-acyl- and 3'- or 4'-O-acyl-cis-dihydroseselins (8-21) and 3',4'-trans-dihydrose ... Full text Link to item Cite

Control of Dispersity and Stereochemistry in Free Radical Telomerizations: A Radical Addition, Cyclization, Chain Transfer (ACT) Strategy

Journal Article Journal of the American Chemical Society · November 1, 1994 A general strategy for the stereoselective preparation of n = 2 telomers displaying narrow dispersity is reported. Covalent assemblies composed of a rigid base compound, flexible tethers, and oxazolidine acrylamide monomers were reacted under free radical ... Full text Cite

Conformational analysis, pharmacophore identification, and comparative molecular field analysis of ligands for the neuromodulatory sigma 3 receptor.

Journal Article Journal of medicinal chemistry · November 1994 Molecular modeling studies were carried out on a series of 1-phenyl-3-amino-1,2,3,4-tetrahydronaphthalenes (phenylaminotetralins, PATs), several PAT structural analogs, and various non-PAT ligands that demonstrate a range of affinities for a novel sigma 3 ... Full text Cite

Synthesis and Characterization of Neopentylindium Compounds: X-ray Crystal Structures of [(Me3CCH2)2InAs(SiMe3)2]2 and (Me3CCH2)2InAs(SiMe3)2In(CH2CMe3)2Cl

Journal Article Organometallics · September 1, 1994 The 1:1 and 2:1 mole ratio reactions of (Me3CCH2)2InCl with As(SiMe3)3 yield the dimeric and mixed-bridging compounds [(Me3CCH2)2InAs(SiMe3)2]2 (1) and (Me3CCH2)2InAs(SiMe3)2-In(CH2CMe3)2Cl (2), respectively. 1 and 2 were characterized by melting point, 1H ... Full text Cite

On the synthesis of mixed-metal and mixed-pnicogen 13–15 ring systems

Journal Article Phosphorus, Sulfur, and Silicon and the Related Elements · August 1, 1994 Several pathways toward the synthesis of mixed-metal and mixed-pnicogen 13–15 ring systems have been explored. Equilibration reactions have proven successful toward the preparation of the latter compounds while most attempts to prepare mixed-metal compound ... Full text Cite

Isolation and Characterization of an Indium-Mixed-Pnicogen Four-Membered-Ring Compound: Crystal Structure of (Me3SiCH2)2InAs(SiMe3)2In(CH2SiMe3)2P(SiMe3)2

Journal Article Organometallics · June 1, 1994 The first four-membered ring containing two indium atoms with bridging by two different group 15 elements, (Me3SiCH2)2InAs(SiMe3)2In(CH2SiMe3)2P(SiMe3)2 (1), to be characterized completely was prepared by the equilibration of [(Me3SiCH2)2lnP(SiMe3)2]2 (2) ... Full text Cite

Plant antitumor agents. 31. The calycopterones, a new class of biflavonoids with novel cytotoxicity in a diverse panel of human tumor cell lines.

Journal Article Journal of medicinal chemistry · May 1994 Three new biflavonoids to which we have accorded the trivial names calycopterone (1), isocalycopterone (2), and 4-demethylcalycopterone (3) and the known flavone 4',5-dihydroxy-3,3',6,7-tetramethoxyflavone (4) were isolated as cytotoxic constituents from t ... Full text Cite

Polymerization and Telomerization of Chiral Acrylamides

Journal Article Journal of Organic Chemistry · March 1, 1994 The acrylamide derived from Oppolzer's camphor sultam was polymerized and the resulting polymer was converted to poly (allyl acetate) through a reduction-acetylation sequence. The poly(allyl acetate) thus obtained was analyzed by NMR and was compared with ... Full text Cite

New modified labdane diterpenoids from cluytia richardiana

Journal Article Journal of Natural Products · February 1, 1994 The aerial parts of Cluytia richardiana yielded two new labdane-type diterpenoids, named cluytene A [3] and cluytene B [4]. The structural assignments and relative stereochemistry of both compounds were established from 2D nmr spectral data and by X-ray cr ... Full text Cite

Preparation, Characterization and Facile Thermolysis of [X2GaP(SiMe3)2]2 (X = Br, I) and (Cl3Ga2P)n: New Precursors to Nanocrystalline Gallium Phosphide

Journal Article Chemistry of Materials · January 1, 1994 [Br2GaP(SiMe3)2]2 and [I2GaP(SiMe3)2]2 have been prepared by the 1:1 mole ratio reaction of the corresponding gallium (III) halide with (Me3Si)3P. Direct introduction probe mass spectrometry indicates that the former product is dimeric in the gas phase; si ... Full text Cite

X-ray crystal structures of [(Me3SiCH2)2InCl]2 and [(Me3SiCH2)InCl2]∞

Journal Article Polyhedron · January 1, 1994 The solid-state structures of ((Me3SiCH2)2InCl (I) and (Me3SiCH2)InCl2 (II) have been determined by single-crystal X-ray analysis. Compound I crystallizes as a centrosymmetric dimer, [(Me3SiCh2)2InCl]2, whilst compound II crystallizes as an infinite polyme ... Full text Cite

Synthesis and characterization of aluminium-phosphorus adducts: X-ray crystal structures of Cl3Al·P(SiMe3)3·C7H8 and Br3Al·P(SiMe3)3·C7H8

Journal Article Polyhedron · January 1, 1994 The attempted dehalosilylation reactions between AlX3 (X = Cl, Br) and P(SiMe3)3 in toluene in 1:1 mole ratios afforded only the adducts Cl3Al·P(SiMe3)3 (I) and Br3Al·P(SiMe3)3 (II), respectively. Compounds I and II were characterized by 1H, 13C, 27Al, and ... Full text Cite

Modified labdane diterpenoids from Cluytia richardiana

Journal Article Phytochemistry · January 1, 1994 The aerial parts of Cluytia richardiana yielded three new modified labdane diterpenoids, named cluytene C, D and E. The structural assignments of the diterpenoids were based on 1H and 13C NMR spectroscopic studies, mainly 2D NMR experiments, including homo ... Full text Cite

Synthesis and molecular structures of R(Me3CCH2)2In · E(SiMe3)3 (R=Me3CCH2, E = P or As; R = Me, E = P).

Journal Article Polyhedron · January 1, 1994 Combining P(SiMe3)3 or As(SiMe3)3 with (Me3CCH2)3In in a 1:1 mole ratio yields simple adducts (Me3CCH2)3In·P(SiMe3)3 (I) and (Me3CCH2)3In·As(SiMe3)3 (II), respectively. Addition of (Me3CCH2)2InCl to a diethyl ether solution of LiP(SiMe3)2 produces Me(Me3CC ... Full text Cite

Synthesis and pharmacological evaluation of 1-phenyl-3-amino-1,2,3,4-tetrahydronaphthalenes as ligands for a novel receptor with sigma-like neuromodulatory activity.

Journal Article Journal of medicinal chemistry · August 1993 Certain novel 1-phenyl-3-amino-1,2,3,4-tetrahydronaphthalenes (1-phenyl-3-aminotetralins, PATs) produced stimulation (ca. 30% above basal levels) of tyrosine hydroxylase (TH) activity at 0.1 microM concentrations in rodent brain tissue. This effect on TH w ... Full text Cite

The stereoselective synthesis of succinamide derivatives via enolate oxidative coupling

Journal Article Tetrahedron Letters · July 9, 1993 Enolates derived from optically pure oxazolidines couple with high stereoselectivity when oxidized with iodine or cupric salts. © 1993. ... Full text Cite

Total synthesis and absolute stereochemistry of the antifungal dipeptide Sch 37137 and its 2S,3S - isomer

Journal Article Tetrahedron Letters · May 14, 1993 The absolute stereochemistry of the epoxide moiety in Sch 37137 has been established as 2R, 3R by its synthesis from L-tartaric acid. . © 1993. ... Full text Cite

Antitumor agents. 139. Synthesis and biological evaluation of thiocolchicine analogs 5,6-dihydro-6(S)-(acyloxy)- and 5,6-dihydro-6(S)-[(aroyloxy)methyl]-1,2,3-trimethoxy-9-(methylthio)-8H- cyclohepta[a]naphthalen-8-ones as novel cytotoxic and antimitotic agents.

Journal Article Journal of medicinal chemistry · March 1993 A series of novel thiocolchicine analogs, 5,6-dihydro-6(S)-(acyloxy)-and 5,6-dihydro-6(S)-[(aroyloxy)-methyl]-1,2,3-trimethoxy-9-(methylthi o)-8H- cyclohepta[a]naphthalen-8-ones, possessing a six-membered ring B, have been synthesized and evaluated for the ... Full text Cite

Preparation and characterization of New C-11 oxygenated artemisinin derivatives

Journal Article Journal of Natural Products · January 1, 1993 Anhydrodihydroartemisinin [2], a potent antimalarial sesquiterpene endoperoxide, was converted to 11-hydroxyartemisinin [4], 11-hydroxy-11-epi-anemisinin [5], a ketone derivative 7 of artemisinin, and an enol ether epoxide 8. Compounds 4, 5, 7, and 8 were ... Full text Cite

Dehalosilylation reactions involving E(sime3)3 and Ph2Incl. Synthesis and X-ray structures of [Ph2Ine(SiMe3)2]2 (E = P or As)

Journal Article Polyhedron · January 1, 1993 Combining P(SiMe3)3 or As(SiMe3)3 with Ph2InCl in a 1:1 mole ratio results in the elimination of Me3SiCl via a dehalosilylation reaction to yield [Ph2InP(SiMe3)2]2 (I) and [Ph2InAs(SiMe3)2]2 (II), respectively. X-ray structures were determined for I and II ... Full text Cite

Free Radical Macrocyclizations from Steroid-Derived Precursors

Journal Article Journal of Organic Chemistry · January 1, 1993 Stereoselective free radical addition reactions were studied using steroid-derived templates in an attempt to control product dispersity. Templates were prepared from bifunctional steroids appropriately substituted with initiating and terminating functiona ... Full text Cite

X-Ray Crystal Structure of an Organoindium Alkoxide Dimer, (Ph2InOSiMe3)2

Journal Article Journal of Coordination Chemistry · January 1, 1993 The solid-state structure of (Ph2InOSiMe3)2, 1. has been established by single-crystal X-ray analysis. Monoclinic crystals of 1 belong to space group P21/c, with a = 9.136(1), b = 15.503(2), c = 11.836(1) A, β= 102.46(1)°, Z = 2. Refinement of atomic param ... Full text Cite

X-ray crystal structure of InCl3·2THF, a neutral five-coordinate bis-adduct of an indium(III) trihalide

Journal Article Polyhedron · January 1, 1993 The 2 : 1 mole ratio reaction of InCl3 and P(SiMe3)3 in a toluene/THF mixture was investigated. The reaction appears to occur in a 1 : 1 mole fashion, since the products obtained are unreacted InCl3 (48.5% recovered) as InCl3·2THF and a fine powder which a ... Full text Cite

Novel Syntheses of Tricyclic, N-Aryl, Pyridine- and Pyrazine-Fused Pyrimidones

Journal Article Collection of Czechoslovak Chemical Communications · 1993 2-methylthio-2-imidazoline and 2-methylthio-1,4,5,6-tetrahydro-2-pyrimidine amidated 2-chloro-3-pyridine- and 2-chloro-3-pyrazinecarbonyl chlorides. The products reacted with aromatic amines forming a series of tricyclic, linearly fused Full text Cite

Synthesis, Characterization, and Thermal Decomposition of [Cl2GaP(SiMe3)2]2, a Potential Precursor to Gallium Phosphide

Journal Article Organometallics · January 1, 1993 [Cl2GaP(SiMe3)2]2 (1) has been prepared from the 1:1 reaction of GaCl3 with P(SiMe3)3. Thermal decomposition of 1 produces a brown powder which contains GaP, as evidenced by an X-ray powder pattern and partial elemental analysis. Compound 1 crystallizes in ... Full text Cite

Neocleordane diterpenoids and their artifacts from Teucrium olivarianum

Journal Article Journal of Natural Products · January 1, 1993 The aerial parts of Teucrium oliverianum yielded five new neocleordane diterpenoids (teucrolins A [4], B [5], C [6], D [7], and E [8]), three neocleordane diterpene artifacts (12-O-methylteucrolivin A [9], 12-O-methylteucrolin A [10], and 12-O-ethylteucrol ... Full text Cite

New Diterpenes from Psiadia Arcabica

Journal Article Phytochemistry · 1993 Cite

Synthesis and absolute configuration of hydroxythreonine, a biosynthetic precursor of rhizobitoxine in pseudomonas

Journal Article Bioorganic and Medicinal Chemistry Letters · January 1, 1993 The synthesis of hydroxythreonine via osmylation of vinyl glycine has permitted a crystalline derivative to be prepared as well as comparison with naturally-derived material, allowing the assignment of the absolute configuration of the natural product as ( ... Full text Cite

Novel, stereoselective syntheses of penem antibiotics: efficient, formal syntheses of SCH 34343

Journal Article Bioorganic and Medicinal Chemistry Letters · January 1, 1993 Novel, stereoselective syntheses of (3S, 4R, 5R)-1-(allyloxycarbonyl)methyl-3-[1-hydroxyethyl]-4-β-naphthoxy(thi ocarbonyl)thio-2-azetidinone (13) and (3S, 4R, 5R, 3′S, 4′R, 5′R)-4,4′-dithio-bis-1-(allyloxy-carbonyl)methyl-3-[-1-hydro xyethyl]-2-azetidinon ... Full text Cite

Synthesis, x-ray structural determination and coordination chemistry of 4′-ferrocenyl-2,2′:6′,2″-terpyridine

Journal Article Polyhedron · January 1, 1993 4′-Ferrocenyl-2,2′:6′,2″-terpyridine(Fctrpy) has been prepared from ferrocene carboxaldehyde and 2-acetylpyridine. A single crystal X-ray structure analysis indicates typical bond distances and angles with nearly coplanar aromatic rings. The angle between ... Full text Cite

Aluminum-Phosphorus Chemistry: Preparation and Structural Characterization of [Et2AlP(SiMe3)2]2, Et(Cl)2Al·P(SiMe3)3, and i-Bu2(Cl)Al·P(SiMe3)3

Journal Article Organometallics · January 1, 1993 Reactions of R2AlCl (R = Et, i-Bu) and EtAlCl2 with P(SiMe3)3 and LiP(SiMe3)2 were studied to investigate the potential use of dehalosilylation and lithium chloride elimination reactions for the preparation of compounds containing either [formula omitted] ... Full text Cite

Synthesis and Characterization of Trimethylsilyl Phosphide Derivatives of Dineopentylindium Chloride. X-ray Crystal Structures of [Me(Me3CCH2)InP(SiMe3)2]2, [formula omitted] and [formula omitted]

Journal Article Organometallics · January 1, 1993 Three new neopentylindium compounds, [Me(Me3CCH2)InP(SiMe3)2]2 (1), [formula omitted] (.2), and [formula omitted] (3), are reported. Dimer 1 contains two different exocyclic alkyl ligands on the group 13 center and is the only product isolated from the rea ... Full text Cite

Unexpected synthesis of trans-2,3-dimethoxy-3-(p-formylphenylamino)- 4′-nitroflavanones

Journal Article Journal of the Chemical Society, Chemical Communications · December 1, 1992 The reaction of o-hydroxyacetophenones 1a-c with p-nitrobenzaldehyde in aqueous methanolic KOH leads to the formation of trans-2,3-dimethoxy-3-(p- formylphenylamino)-4′-nitroflavanones 2a-c, two of which have been structurally characterized by X-ray crysta ... Full text Cite

Sch 47918: A Novel PAF Antagonist from the Fungus Phoma Sp

Journal Article Journal of Organic Chemistry · October 1, 1992 A novel platelet activating factor (PAF) antagonist, Sch 47918, was isolated from the fermentation broth of the fungus, Phoma sp. The structure of this compound was elucidated by spectroscopic methods. The proposed structure and stereochemistry of Sch 4791 ... Full text Cite

Antitumor agents, 135. Structure and stereochemistry of polacandrin, a new cytotoxic triterpene from Polanisia dodecandra.

Journal Article Journal of natural products · October 1992 A new dammarane triterpene, polacandrin [1], has been isolated from Polanisia dodecandra. The structure of 1 was established as 1 beta, 3 alpha, 12 beta, 25-tetrahydroxy-20(S),24(S)-epoxydammarane by chemical and spectroscopic methods, which included the c ... Full text Cite

Origins of Stereoselectivity in Radical Additions: Reactions of Alkenes and Radicals Bearing Oxazolidine and Thiazolidine Amide Groups

Journal Article Journal of the American Chemical Society · September 1, 1992 Single-crystal X-ray analysis of four alkenes that undergo stereoselective radical addition reactions are reported. The facial selectivity of radical additions to these alkenes is understood based upon their solid-state conformations. Alkenes which have a ... Full text Cite

Solid state thermal degradation products of rosaramicin.

Journal Article The Journal of antibiotics · September 1992 Full text Cite

Reaction of LiE(SiMe3)2 with Compounds Containing Four-Membered Cores of the General Formula MEM(Cl) (M = In, E = As, P; M = Ga, E = As): Novel Rearrangement Reactions to Form the Adducts R3M.As(SiMe3)3 (R = Me3SiCH2, M = In; R = Ph, M = Ga)

Journal Article Organometallics · July 1, 1992 The 1:1 reactions of R2ME(SIMe3)2M(R)2CI with LIE(SIMe3)2(R = Me3SiCH2, = In, E = P; R = Me3SiCH2, = In, E = As; R = Me3SICH2, M = Ga, E = As; R = Ph, M = Ga, E = As) result in the formation of species containing MEME core structures as verified by compari ... Full text Cite

Synthesis of (+)-8-methyl cercosporamide: Stereochemical correlation of natural (-)-cercosporamide with (+)-usnic acid

Journal Article Tetrahedron · June 5, 1992 The absolute configuration of the antifungal antibiotic cercosporamide was established as C-9b-(-)-(S) by correlation with synthetic (+)-8-methylcercosporamide. This was accomplished via conversion of the isoxazole (6) available from (+)-usnic acid. Struct ... Full text Cite

Synthesis and Characterization of Novel Aluminum-Arsenic Compounds. Crystal Structure of [Et2AlAs(SiMe3)2]2

Journal Article Organometallics · February 1, 1992 The viability of dehalosilylation and lithium chloride elimination reactions for use in the preparation of compounds containing core rings of the type Al-As-Al-As and Al-As-Al-Cl was investigated. The second fully characterized aluminum-arsenic dimer, [Et2 ... Full text Cite

Synthesis of Corticoids from 9α-Hydroxyandrost-4-ene-3,17-dione

Journal Article Journal of Organic Chemistry · January 1, 1992 The synthesis of 17α,21-bis(acetyloxy)-16β-methylpregna-4,9(11)-diene-3,20-dione (24) from the sterol-derived 9α-hydroxyandrost-4-ene-3,17-dione (1) has been completed. The key steps in the synthesis are 16β-methylation and conversion of the 17-ketone to 1 ... Full text Cite

Bisabolene and guaiane sesquiterpenes from Pulicaria glutinosa

Journal Article Phytochemistry · January 1, 1992 Aerial parts of Pulicaria glutinosa yielded three bisabolene sesquiterpenes, puliglutol, puliglutal and puliglutone; structural assignments were based largely on their 2D NMR spectral data. A fourth sesquiterpene, the guaiane cyclo-epoxypuliglene, was also ... Full text Cite

The resolution, isolation, and pharmacological characterization of the enantiomers of a benzamide containing a chiral sulfoxide.

Journal Article Chirality · January 1992 Rac-ML-1035 (MDL 201,035: 4-amino-5-chloro-2-[2-(methylsulfinyl)ethoxy]-N-[2-(diethylamino)ethyl] benzamide hydrochloride) is a racemic gastroprokinetic with serotonergic (5-hydroxytryptamine, 5-HT) activity and a novel chiral sulfoxide substituent. Chroma ... Full text Cite

A flavone and diterpene from Psiadia arabica

Journal Article Phytochemistry · January 1, 1992 The aerial parts of Psiadia arabica yielded two new constituents: a flavone, 5,7,3′-trihydroxy-2′,4′,5′-trimethoxyflavone, the structure of which was derived from spectral data and chemical derivatization, and a kaurane diterpene named psiadian, which was ... Full text Cite

Synthesis and Structural Characterization of Organoindium-Phosphorus Complexes Containing a Four-Membered In-P-In-Cl or In-P-In-P Ring: Crystal Structures of (Me3SiCH2)2InP(SiMe3)2In(CH2SiMe3)2Cl and [(Me3SiCH2)2InP(SiMe3)2]2

Journal Article Organometallics · January 1, 1992 The first example of an (formula omitted)-ring-containing compound, (formula omitted) (1), was prepared by the reaction of (Me3SiCH2)2InCl and (Me3Si)3P in a 2:1 mole ratio. Similarly, the dimer containing an (formula omitted) core, [(Me3SiCH2)2InP(SiMe3)2 ... Full text Cite

Synthesis, structural characterization, and reactivity of (Me3CCH2)2GaAs(SiMe3)2Ga(CH2CMe3)2Cl, [(Me3CCH2)2GaAs(SiMe3)2]2, and (Me3CCH2)2Ga(Cl)•As(SiMe3)3

Journal Article Organometallics · January 1, 1992 Reaction of 2 equiv of (Me3CCH2)2GaCl with (Me3Si)3As affords (formula omitted) (1), the fourth example of a compound containing the Ga-As-Ga-X (X = Cl, Br) core, but the first wherein the organogallium four-membered ring with arsenic/halogen mixed bridgin ... Full text Cite

Synthesis and characterization of compounds containing the As(SiMe3)2 bridging group: Crystal structures of [tBu2GaAs(SiMe3)2]2 and tBu2GaAs(SiMe3)2Ga(tBu)2Cl

Journal Article Polyhedron · January 1, 1992 tBu2GaCl reacts with LiAs(SiMe3)2·2thf (1:1 mole ratio) to yield I, which on reaction with tBu2GaCl (1:2 mole ratio) affords II quantitatively. [tBu2GaAs(SiMe3)2]2 (I) and tBu2GaAs(SiMe3)2Ga(tBu)2Cl (II) were not produced from reaction mixtures of tBu2GaCl ... Full text Cite

Rearrangements of methyl 9β-hydroxy-11-oxo-(-)-kauran-19-oate to diterpene skeletons with new ring systems

Journal Article Tetrahedron Letters · December 23, 1991 On treatment with boron trifluoride etherate-acetic anydride-acetic acid, the 9β-hydroxy-11-oxo derivative 1c of methyl(-)-kaur-9(11)-en-19-oate did not form a pinacolic type of rearrangement product (B-homo derivative), but instead it yielded compounds 2 ... Full text Cite

Studies Directed at the Synthesis of Optically Active Pretazettine via Intramolecular Nitrone/Alkene Cycloaddition Reactions

Journal Article Journal of Organic Chemistry · November 1, 1991 A protocol for the synthesis of optically active pretazettine which focuses on both the control of relative stereochemistry between the angular aryl and C6a hydroxyl groups and absolute stereochemistry has been developed and executed. The synthesis of the ... Full text Cite

Total Synthesis of Griseolic Acid Derivatives from D-Glucose

Journal Article Journal of Organic Chemistry · November 1, 1991 Griseolic acid, 1, is a potent nonselective cyclic nucleotide-phosphodiesterase inhibitor isolated from Streptomyces Griseoaurantiacus. Recently, preparation of several griseolic acid derivatives, including 3, has been reported. We have completed the chira ... Full text Cite

Diastereoselective diels-alder reactions between substituted 1,3-butadienes and n-α-methylbenzylmaleimide

Journal Article Tetrahedron Letters · October 14, 1991 The TiCl4 catalyzed reaction between 2-t-butyl-1,3-butadiene and N-α-methylbenzylmaleimide at -65°C affords diastereomeric Diels-Alder adducts in a 15:1 ratio. The structure of the major adduct was determined by x-ray. © 1991. ... Full text Cite

Free-Radical Telomerization of Chiral Acrylamides: Control of Stereochemistry in Additions and Halogen-Atom Transfer

Journal Article Journal of the American Chemical Society · August 1, 1991 The free-radical reactions of carbon radicals substituted α to a chiral pyrrolidine amide have been studied. The pyrrolidine used was 2,5-dimethylpyrrolidine, available as either the R,R or S,S enantiomer from d- or l-alanine, and the radicals were generat ... Full text Cite

Chelation of 2-Substituted-1-lithoxides: Structural and Energetic Factors of Relevance to Synthetic Organic Chemistry

Journal Article Journal of the American Chemical Society · July 1, 1991 A number of lithium 2-(methylamino)-, 2-(dimethylamino)-, 2-methoxy-, and 2-(isopropylthio)-substituted-l-phenyl-1-propoxides were studied as models for asymmetric synthetic strategies for which lithium chelation between two electronegative atoms has frequ ... Full text Cite

Synthesis and Characterization of Indium-Arsenic Compounds Containing a Four-Membered In-As-In-As or In-As-In-Cl Ring: Crystal Structures of [(Me3SiCH2)2InAs(SlMe3)2]2 and (Me3SiCH2)2InAs(SiMe3)2In(CH2SiMe3)2Cl

Journal Article Organometallics · July 1, 1991 The first four-membered ring compounds with bridging of the indium atoms by two arsenic atoms and with mixed bridging of the indium centers by one arsenic and one chlorine, [(Me3SiCH2)2lnAs(SiMe3)2]2 (1) and (Me3SiCH2)2lnAs(SiMe3)2ln(CH2SiMe3)2Cl (2), to b ... Full text Cite

Synthesis, Structure, and Properties of a 2-(Trimethylsilyl)cyclobutenocyclooctatetraene

Journal Article Journal of the American Chemical Society · June 1, 1991 The first example of the cyclobutenocyclooctatetraene structural class (2) to possess stability at room temperature has been prepared by a route involving ring contraction via a Wolff rearrangement. Derivatives have been characterized by various spectrosco ... Full text Cite

Controlling benzylic functionality and stereochemistry: 1. Synthesis of the secopseudopterosin aglycone

Journal Article Tetrahedron Letters · May 6, 1991 Directed, homogeneous hydrogenation of 1-(1-hydroxymethylethyl)-5-methoxy-3,4-dihydronaphthalene (7), followed by protection and selective benzylic oxidation gave the 1-oxo-(4R*, 11R*) compound (13). After addition of MeCeCl2, the natural C-1 stereochemist ... Full text Cite

Synthesis and characterization of gallium-arsenic compounds containing a four-membered GaAsGaCl or GaAsGaAs ring: crystal structures of (Me3SiCH2)2GaAs(SiMe3)2Ga(CH2SiMe3)2Cl and [(Me3SiCH2)2GaAs(SiMe3)2]2

Journal Article Journal of Organometallic Chemistry · April 9, 1991 The third example of an organogallium four-membered ring compound with arsenic, halogen mixed bridging, (Me3SiCH2)2GaAs(SiMe3)2Ga(CH2SiMe3)2Cl (1), was prepared by the reaction of (Me3Si)3As (2) with two equivalents of (Me3SiCH2)2GaCl. X-ray crystallograph ... Full text Cite

Competition rate constants for addition of cyclohexyl radical to amide substituted alkenes: origins of acyclic stereoselection in radical additions

Journal Article Tetrahedron Letters · February 4, 1991 Competition rate constants were determined for the addition of cyclohexyl radical to α,β unsaturated amides derived from pyrrolidine and trans-2,5-dimethylpyrrolidine. The relative rates can be understood by single crystal X-Ray analyses of the alkenes and ... Full text Cite

Photochemical Reaction of a Diplatinum μ-Phenylethenylidene Complex with Diphenylacetylene: Unusual Formation of a μ-η1:η3-Butadienediyl Complex

Journal Article Organometallics · February 1, 1991 Photochemical reaction of a diplatinum μ-alkenylidene complex with PhC≡CPh occurs with C-C coupling of the alkenylidene and alkyne moieties to give an expanded, unsaturated μ-η1:η3-butadienediyl ligand. Structural and isotopic-labeling studies indicate tha ... Full text Cite

Transformation of O2S(C≡CCMe3)2 to an exoalkylidene thiete 1,1-dioxide ligand by Pt-H addition and rearrangement reactions

Journal Article Journal of the Chemical Society, Chemical Communications · December 1, 1990 Addition of a Pt-H bond to the C≡C bond of an alkynyl substituent of a dialkynylsuiphone occurs regioselectively to give an exoalkylidene thiete 1, 1-dioxide ligand following a subsequent insertion and rearrangement of the second alkynyl substituent; a pro ... Full text Cite

Intramolecular 1,3-dipolar cycloaddition of a nitrone derived from 3-O-allyl-D-(+)-glucose: An expedient synthesis of a chiral oxepane derivative

Journal Article Journal of the Chemical Society, Chemical Communications · December 1, 1990 The intramolecular 1,3-dipolar cycloaddition of the N-benzylnitrone of 3-O-allyl-D-(+)-glucose yielded a chiral oxepane derivative 2, potentially useful for the synthesis of other chiral systems. ... Full text Cite

Electrochemical Oxidative Addition Involving Dirhodium(I) Complexes Containing Transoid Bridging Bis(diphenyIphosphino)methane Ligands. Crystal Structure of a Dirhodium(II) Complex with an Unusual Folding of the Diphosphine Ligand

Journal Article Inorganic Chemistry · July 1, 1990 The two-electron electrochemical oxidation of complexes such as [Rh2(μ-dppm)2(r-BuNC)2(μ-A)]PF6 (dppm = bis(diphenylphosphino)methane; A = pyrazolate derivative) is facilitated by the presence of neutral Lewis bases such as pyridine derivatives or anionic ... Full text Cite

Rabbit and human liver contain a novel pentacyclic triterpene ester with acyl-CoA: cholesterol acyltransferase inhibitory activity.

Journal Article The Journal of biological chemistry · May 1990 Acyl-coenzyme A (CoA):cholesterol acyltransferase (ACAT) catalyzes the intracellular fatty acid esterification of cholesterol and is thought to play a key role in lipoprotein metabolism and atherogenesis. Herein we describe the purification and characteriz ... Full text Cite

Synthesis and dopamine agonist properties of (+-)-trans-3,4,4a,10b-tetrahydro-4-propyl-2H,5H-[1]benzopyrano [4,3-b]-1,4-oxazin-9-ol and its enantiomers.

Journal Article Journal of medicinal chemistry · January 1990 The dopamine agonist profile of (+-)-trans-3,4,4a,10b-tetrahydro-4-propyl-2H,5H-[1]benzopyrano [4,3-b]-1,4-oxazin-9-ol (16a) and its enantiomers (16b-c) was examined. Racemic 16a exhibited moderate affinity for the dopamine (DA) D2 receptor labeled with th ... Full text Cite

Conversion of Artemisinin to Artemisitene

Journal Article Journal of Natural Products · January 1990 Full text Cite

Highly stereoselective radical addition to a trisubstituted alkene by low temperature photolysis of thiohydroxamic esters

Journal Article Tetrahedron Letters · January 1, 1990 Low temperature carbon radical addition to α,β-unsaturated amides of trans-2,5-dimethylpyrrolidine was achieved in high yield with high diastereoselectivity by photolysis of Barton esters. Use of an olefin substituted with three electron withdrawing groups ... Full text Cite

Two Germacrane Sesquiterpenes from Pulicaria glutinosa

Journal Article Phytochemistry · 1990 Cite

Structure and stereochemistry of pseudolarolide-H, a novel peroxy triterpene dilactone from Pseudolarix kaempferi

Journal Article Tetrahedron Letters · January 1, 1990 A novel peroxy triterpene dilactone, pseudolarolide-H, has been isolated from the seeds of Pseudolarix kaempferi, and its structure and stereochemistry have been established from spectral data and single-crystal X-ray analysis. © 1990. ... Full text Cite

Stereospecific synthesis of the aglycone of pseudopterosin E

Journal Article Pure and Applied Chemistry · January 1, 1990 Aglycone 1_ of pseudopterosin E has been synthesized from the tetralone 2 using several novel reactions to control stereselecti vi t.y. © 1990 IUPAC ... Full text Cite

X-ray Crystal Structure of Lygodinolide: A Novel Spiro Furopyran-Perhydrophenanthrene Derivative from Lygodium flexuosum

Journal Article Journal of Organic Chemistry · January 1, 1990 In a previous paper,1 we reported the structure elucidation of O-p-coumaryl dryocrassol, a new compound isolated along with the known compounds tectoquinone, kaempferol, kaempferol-3-β-D-glucoside, β-sitosterol, stigmasterol, and dryocrassol itself from Ly ... Full text Cite

Macrolactams: a New Class of Antifungal Agents

Journal Article J. Amer. Chem. Soc. · 1990 Cite

Structure of bisosthenon, a novel dimeric coumarin from Citrus plants.

Journal Article Chemical and Pharmaceutical Bulletin · 1990 Full text Cite

Decomposition of dihydroartemisitene on silica gel

Journal Article Journal of Natural Products · January 1, 1990 Dihydroartemisitene [5], obtained by reducing its hydroperoxy analogue with triphenylphosphine, was found to undergo isomerization to the keto-aldehyde 6 when chromatographed on Si gel. X-ray crystallographic analysis established the structure of each comp ... Full text Cite

Structural and Energetic Evidence for O-Li-N Chelation in a Model for Asymmetric Induction

Journal Article Journal of the American Chemical Society · January 1, 1990 Full text Cite

Revision of the stereochemistry of (+)-tuberine, an alkaloid from Haplophyllum tuberculatum

Journal Article Phytochemistry · January 1, 1990 The structure of the alkaloid (+)-tuberine, isolated from Haplophyllum tuberculatum, has been revised to N-benzoyl-4′-[(2″S,3″R,6″R)-(+)-7″-acetoxy-2″-hydroxy-3″,7″-dimethyl-3″,6″-epoxyoctyloxy]-phenethylamine on the basis of an X-ray crystallographic stud ... Full text Cite

Evidence for a Bis(alkylidene)silacyclopropane Intermediate in the Platinum-Mediated Formation of a Silacyclobutene

Journal Article Journal of the American Chemical Society · January 1, 1990 When Ph2Si(C≡CCMe3)2 is treated with a cationic Pt-H reagent, a 4-alkylidene-1-silacyclobutenyl ring system is formed. Evidence for the presence of two intermediates in this reaction sequence is obtained by using selective trapping reactions. Acetic acid c ... Full text Cite

Preparation and chemistry of Me3SiCH2AsH2; Preparation of [Me3SiCH2(H)AsGaPh2]3, a trimeric mono(arsino)gallane containing a hydrogen bonded to arsenic. Isolation and X-ray crystal structure of (Me3SiCH2As)5

Journal Article Polyhedron · January 1, 1990 Reduction of Me3SiCH2AsCl2 (I) with LiA1H4 at -78°C afforded Me3SiCH2 AsH2 (II) and reaction of II with Ph3Ga produced [Me3SiCH2(H)AsGaPh2]3 (III) which was characterized by partial elemental analysis (C and H), 1H NMR spectroscopy and a cryoscopic molecul ... Full text Cite

X-ray crystal structure of acrovestone, a cytotoxic principle from Acronychia pedunculata.

Journal Article Journal of natural products · November 1989 Acrovestone was isolated from the stem and root back of Acronychia pedunculata and shown for the first time to be a cytotoxic principle. Its structure, derived from spectral data, was completely characterized by single-crystal X-ray analysis. ... Full text Cite

Experimental, Structural, and Theoretical Studies of Diplatinum Complexes Containing Bridging Phenylethenylidene Ligands Including the Excited-State Chemistry and Photophysics of Photochemically Generated Species

Journal Article Organometallics · October 1, 1989 The results of a comprehensive investigation of the chemistry of the diplatinum compound [Pt2(μ-C=CHPh) (C≡CPh) (PEt3)4]BF4(1) and related derivatives are presented. Complex 1 reacts with halides, NCS-, and various RS-nucleophiles to give the neutral compo ... Full text Cite

Plant antimutagenic agents, 7. Structure and antimutagenic properties of cymobarbatol and 4-isocymobarbatol, new cymopols from green alga (Cymopolia barbata).

Journal Article Journal of natural products · September 1989 Two new compounds, cymobarbatol and 4-isocymobarbatol, were isolated from the marine alga Cymopolia barbata. The complete structures and absolute stereochemistries of these compounds were elucidated by a variety of spectroscopic techniques and X-ray crysta ... Full text Cite

Synthesis and receptor affinities of some conformationally restricted analogues of the dopamine D1 selective ligand (5R)-8-chloro-2,3,4,5-tetrahydro-3-methyl-5-phenyl- 1H-3-benzazepin-7-ol.

Journal Article Journal of medicinal chemistry · August 1989 The synthesis of a structurally novel series of 6,6a,7,8,9,13b-hexahydro-5H-benzo[d]naphtho[2,1-b]azepines (2), conformationally restricted analogues of the dopamine D1 antagonist (5R)-8-chloro-2,3,4,5-tetrahydro-3-methyl-5-phenyl-1H-3-benzazepin -7-ol (SC ... Full text Cite

Prostate. III--A structural feature characteristic of the rat prostate 5 alpha-reductase active site.

Journal Article Journal of steroid biochemistry · March 1989 To aid in the design of new inhibitors of steroidal 5 alpha-reductase for treatment of prostate cancer, we have studied the topography of the 5 alpha-reductase active site (5 alpha-R) and of the related androgen (RA) and progesterone (RP) receptors in the ... Full text Cite

X-Ray crystal structure of swertanone, a triterpene of new skeletal type from Swertia chirata Buch.-Ham.

Journal Article Journal of the Chemical Society, Chemical Communications · January 1, 1989 The structure and stereochemistry of swertanone, a triterpene with a new skeletal type isolated from Swertia chirata, have been established from spectral data and single-crystal X-ray analysis. ... Full text Cite

Transformation of a Trialkynylphosphine Oxide to a 2-Alkylidene-1,2 dihydro-3-phosphete P-Oxide Ligand by Pt-H Addition and Rearrangement Reactions. Activation of Molecular Hydrogen by a Platinum(II) Complex

Journal Article Organometallics · January 1, 1989 Addition of the Pt—H bond of [trans-Pt(H)(PEt3)2(THF)]+ to the C≡C triple bond of the alkynyl substituent of O=PPh2(C≡CPh) occurs regioselectively to give a Pt, P μ-alkenylidene complex. Similar addition of a Pt—H bond to the trialkynylphosphine oxide O=P( ... Full text Cite

Cytotoxic Components of Diospyros morrisiana

Journal Article Phytochemistry · 1989 Cite

Synthesis of novel substituted cyclopentadienes and their early transition metal complexes

Journal Article Polyhedron · January 1, 1989 Synthesis of two substituted cyclopentadienes, 1,3-bis(1-methylcyclohexyl) cyclopentadiene, Cp′H and [2-methyl-2-(2-pyridyl)ethyl]cyclopentadiene, Cp″H from fulvene intermediates is reported. These are readily converted to their early transition metal comp ... Full text Cite

Structure and synthesis of murrapanine, a novel skeletal indole-naphthoquinone alkaloid and cytotoxic principal from Murraya paniculata var. omphalocarpa

Journal Article Tetrahedron Letters · January 1, 1989 A novel skeletal cytotoxic indole-naphthoquinone alkaloid, murrapanine, has been isolated from the root bark of Murraya paniculata var. omphalocarpa and its structure has been established from spectral data and single-crystal X-ray analysis; the synthesis ... Full text Cite

A concise route to the oxathiazepine containing eudistomin skeleton and some carba-analogs

Journal Article Tetrahedron Letters · January 1, 1989 The unsubstituted Eudistomin skeleton containing the oxathiazepine D ring was prepared along with a series of unsubstituted and amino-substituted carba-analogs, using an intramolecular Pictet-Spengler condensation. © 1989. ... Full text Cite

Neihymicin, a New Cytotoxic Antibotic fromMicromonospora neihuensis

Journal Article Plant Molecular Biology · 1989 Cite

Boron Analogs of Amino Acids

Journal Article Inorg. Synth. · 1989 Cite

The twist-boat conformation in a gallium-arsenic six-membered ring: crystal structure of [(Me3SiCH2)2AsGaBr2]3

Journal Article Journal of Organometallic Chemistry · October 25, 1988 [(Me3SiCH2)2AsGaBr2]3, the first trimeric mono(arsino)gallane to be structurally characterized by X-ray crystallographic analysis, has been shown to contain a (GaAs)3 ring in the twist-boat conformation. Crystals of the trimer are monoclinic, space group P ... Full text Cite

Yuehchukene Analogues

Journal Article Journal of Organic Chemistry · June 1, 1988 Yuehchukene and the bisnoryuehchukenes have been synthesized by the dimerization of β-(dehydroprenyl) indole and its demethyl derivative, respectively. Several routes of preparation of the monomers were developed. These β-indolyl dienes were used in Diels- ... Full text Cite

Neihumicin, a new cytotoxic antibiotic from Micromonospora neihuensis. II. Structural determination and total synthesis.

Journal Article The Journal of antibiotics · April 1988 The structure of neihumicin, a new antibiotic isolated from the fermentation broth of Micromonospora neihuensis Wu, sp. nov., has been determined as (Z)-3,(Z)-6-dibenzylidene-2-methoxy-3,6-dihydropyrazin-5-one based upon spectral evidence and X-ray crystal ... Full text Cite

Chiral Discrimination in the Structures and Energetics of Association of Stereoisomeric Salts of Mandelic Acid with α-Phenethylamine, Ephedrine, and Pseudoephedrine

Journal Article Journal of the American Chemical Society · March 1, 1988 A carefully coordinated study of the relations between structure and energetics of association in the crystalline state and solution is reported here. Hydrogen-bonded ion pairs formed from reaction between the enantiomers of mandelic acid, α-phenethylamine ... Full text Cite

Equilibration of Diastereomeric Two-Chain Surfactants. Hydrophobic Control of Organic Stereochemistry

Journal Article Journal of the American Chemical Society · March 1, 1988 Four two-chain dicarboxylic acid surfactants linked with a carbonyl group were synthesized and studied. The compounds exist as meso and (±) diastereomers, and they form aggregates, presumably micelles, at concentrations >10−5 M. Equilibration of the diacid ... Full text Cite

Synthesis of desethanoqinghaosu, a novel analogue of the antimalarial qinghaosu

Journal Article Journal of the Chemical Society, Chemical Communications · January 1, 1988 Desethanoqinghaosu, a novel potential antimalarial qinghaosu analogue containing the unique C-O-O-C-O-C-O-C=O (or cyclic peroxide lactone) moiety present in the natural product, has been synthesized from R-(+)-citronellal and its structure and stereochemis ... Full text Cite

A novel synthesis of cis-1-[[6-chloro-3-[(2-chloro-3-thienyl)methoxy]-2,3-dihydrobenzo[b]thien-2-yl]methyl]1h-imidazole. A new class of azole antifungal agents

Journal Article Tetrahedron · January 1, 1988 Ring contraction of cis-3-bromo-7-chloro-3,4-dihydro-2H-1-benzothiopyran-4-ol 4 in the presence of imidazole results in formation of cis-6-chloro-2,3-dihydro-2-(1H-imidazol-1-ylmethyl) benzo[b]thiophene-3-ol 8 as the major product. The structure of 8 was d ... Full text Cite

Structure and stereochemistry of corytensine, a new phthalideisoquinoline alkaloid from Corydalis ochotensis

Journal Article Heterocycles · January 1, 1988 A new phthalideisoquinoline alkaloid, corytensine, has been isolated from Corydalis ochotensis Tarcz., and its structure and stereochemistry have been established as (1) from spectral data and a single crystal X-ray analysis. © 1988. ... Full text Cite

Structures and stereochemistry of melicophyllone A and hypocholesterolemic melicophyllone B, novel sesquiterpene lactones from Melicope triphylla

Journal Article Journal of the Chemical Society, Chemical Communications · January 1, 1988 Melicophyllones A and B, two novel skeletal sesquiterpene lactones, have been isolated from Melicope triphylla and their structures have been established from spectral data in conjunction with single-crystal X-ray analyses; melicophyllone B demonstrated si ... Full text Cite

Ghalakinoside, a cytotoxic cardiac glycoside from Pergularia tomentosa

Journal Article Phytochemistry · January 1, 1988 The isolation and structural elucidation using spectroscopic methods and X-ray analysis of ghalakinoside, a novel cytotoxic cardiac glycoside, containing a doubly linked sugar substituent are reported. Calactin, another related glycoside was also isolated ... Full text Cite

Cardiotonic agents. 8. Selective inhibitors of adenosine 3',5'-cyclic phosphate phosphodiesterase III. Elaboration of a five-point model for positive inotropic activity.

Journal Article Journal of medicinal chemistry · November 1987 Inhibitors of adenosine 3',5'-cyclic phosphate phosphodiesterase III (cAMP PDE III) were studied by using solid-state, solution, and theoretical methods in order to refine a five-point model for positive inotropic activity. Cyclic AMP PDE III inhibitors be ... Full text Cite

Reactions of (Me3SiCH2)2AsSiMe3 with Gallium Halides. Crystal Structure and Dynamic NMR Study of the Dimer {[(Me,SiCH2)2As]2GaBrj2

Journal Article Organometallics · October 1, 1987 (Me3SiCH2)2AsSiMe3reacted with the gallium halides GaBr3, MeGaCl2, and PhGaCl2to produce the (arsino)gallanes [(Me3SiCH2)2AsGaBr2]3, {[(Me3SiCH2)2As]2GaBr}2, [(Me3SiCH2)2AsGaMeCl]n(n = 2, 3), and [(Me3SiCH2)2AsGaClPh]„ (n = 2, 3), which were characterized ... Full text Cite

The Pyranoside Ring as a Nucleophile in Aldol Condensations

Journal Article Journal of Organic Chemistry · July 1, 1987 The enolate derived from a 2-deoxy-3-keto-hexopyranoside undergoes aldol condensations in high yields. With respect to the newly formed bond, the orientation at C2 is always axial, indicating that the pyranoside moiety exerts excellent stereoselectivity at ... Full text Cite

Unusual Reactions of Magnesium Indolates with Benzenesulfonyl Chloride

Journal Article Journal of Organic Chemistry · July 1, 1987 Grignard reagents from N-unsubstituted indoles and benzenesulfonyl chloride undergo reaction such as to produce unstable intermediates of β-chlorination and a-sulfonylation, which are transformed into oxindoles or substituted indoles. In the same reaction, ... Full text Cite

Synthesis and characterization of a dimeric tris(arsino)gallane containing a nonplanar (Ga-As)2 ring: crystal structure of {[(Me3SiCH2)2As]3Ga}2

Journal Article Journal of Organometallic Chemistry · May 12, 1987 The dimer {[(Me3SiCH2)2As]3Ga}2, only the second tris(arsino)gallane to be completely characterized, has been prepared by the reaction of (Me3SiCH2)2AsLi with GaCl3; X-ray crystallographic analysis shows it to be the first example of a compound containing ... Full text Cite

Enantioselectivity in camphor pinacolisation

Journal Article Tetrahedron Letters · January 1, 1987 Total enantioselectivity has been observed in pinacol formation using Li/THF. (+) Camphor and (±) Camphor give the optically active and racemic form of a single pinacol whose stereochemistry has been established as endo:endo by X-ray analysis. An exo:endo ... Full text Cite

Stereoselective Epdxidation of a Pendant Vinyl Group at C3 of a Pyranoside

Journal Article Journal of Carbohydrate Chemistry · September 1, 1986 The epoxidation of a pendant vinyl group, axially oriented at C3 of the pyranoside ring, can be effected with complete diastereofacial selectivity, depending upon whether a free hydroxyl group is located at C2 or C4. © 1986, Taylor & Francis Group, LLC. Al ... Full text Cite

Synthesis and crystal structure of the dimer bis{[bis(trimethylsilylmethyl)arsino]diphenylgallane}

Journal Article Journal of Organometallic Chemistry · July 15, 1986 The dimer [(Me3SiCH2)2AsGaPh2]2, obtained from the reaction of (Me3SiCH2)2AsH with Ph3Ga, has been characterized by partial elemental analysis, NMR spectroscopy, cryoscopic molecular weight determination, and complete single-crystal X-ray analysis. Crystal ... Full text Cite

Rearrangements during Oxidations of the 9-Phosphabicyclo[6.1.0]nona-2,4,6-triene System: Formation of Phosphonin Oxides

Journal Article Journal of the American Chemical Society · July 1, 1986 P-Phenyl and P-tert-butyl derivatives of the title compound react with hydrogen peroxide or tert-butyl hydroperoxide at -15 °C; the C-C bond of the three-membered ring is opened, and the first observable product is the cis,cis,cis,trans-phosphonin oxide. W ... Full text Cite

Antiinflammatory activity of substituted 6-hydroxypyrimido[2,1-f]purine-2,4,8(1H,3H,9H)-triones. Atypical nonsteroidal antiinflammatory agents.

Journal Article Journal of medicinal chemistry · June 1986 A novel class of antiinflammatory drugs, which are substituted derivatives of the fused tricyclic system 6-hydroxypyrimido[2,1-f]purine-2,4,8(1H,3H,9H)-trione, is described. Synthetic procedures and structure determination with the assistance of X-ray crys ... Full text Cite

Antitumor agents, 79. Cytotoxic antileukemic alkaloids from Brucea antidysenterica.

Journal Article Journal of natural products · May 1986 Two cytotoxic antileukemic alkaloids, the new 1,11-dimethoxycanthin-6-one (3) and the known 11-hydroxycanthin-6-one (1), as well as the known canthin-6-one (2) were isolated from the stem of Brucea antidysenterica. The structures of 1-3 were determined fro ... Full text Cite

Stereoisomer Effects on the Paal-Knorr Synthesis of Pyrroles

Journal Article Journal of Organic Chemistry · January 1, 1986 The neurotoxicity of n-hexane has been postulated to result from the reactivity of its γ-diketone metabolite, 2,5-hexanedione (1), with lysyl amino groups of proteins to form pyrroles (Paal-Knorr synthesis). We have synthesized a series of 3,4-disubstitute ... Full text Cite

Isolation and characterization of an organogallium-arsenic cluster: Crystal structure of [(PhAsH)(R2Ga)(PhAs)6(RGa) 4](R=Me3SiCH2)

Journal Article Journal of the Chemical Society (Resumed) · January 1, 1986 [(PhAsH)(R2Ga)(PhAs)6(RGa)4](R=Me 3SiCH2) has been isolated as a product of the reaction of PhAsH2 with (Me3SiCH2)3Ga and determined by X-ray crystallographic analysis to be a cluster containing an As7Ga5 core. ... Full text Cite

Remarkably Facile Synthesis of an Isoelectronic and Isostructural Boron Analogue of Acetylcholine

Journal Article Journal of the American Chemical Society · January 1, 1986 Full text Cite

The synthesis, x-ray crystal structure, and solution characterization of a bis(diphosphine)-bridged dirhodium(I) complex containing a Rh2P4 six-membered ring

Journal Article Journal of the Chemical Society, Dalton Transactions · January 1, 1986 The preparation of [{Rh(cod)}2(μ-L1)2][BF4] 2 (1) from (CH2CMe=CH2P)2 (L1) and [Rh(cod)2]-BF4 (cod = cyclo-octa-1,5-diene) is described. The compound crystallizes in the monoclinic space group P21/c (C52h), with a = 9.650(1), b = 11.609(1), c = 21.884(3) Å ... Full text Cite

Synthesis of Phosphinamides in the 5, 6-Oxaphosphabicyclo[2.2.2]octene Series as Possible Precursors of Metaphosphoramidates

Journal Article Journal of Organic Chemistry · January 1, 1986 The readily dimerizable 1-aminophosphole oxides were found to function as dienes in the Diels-Alder reaction with N-phenylmaleimide, thereby providing phosphinamides with the 7-phosphanorbomene structure. The dimers also possess this structural feature, wh ... Full text Cite

Oxidative addition of aryl sulphides to low-valent nickel species

Journal Article Journal of the Chemical Society, Chemical Communications · January 1, 1986 Exposure of diaryl sulphides to tris(tri-n-butyl)phosphinonickel(0) is shown to lead to oxidative addition products, one of which has been characterized by n.m.r. spectral analysis and another by single-crystal X-ray analysis. ... Full text Cite

Oxidation of methyl podocarpate and methyl 12-hydroxyabietan-8,11,13-trien-18-oate with thallium(III) perchlorate

Journal Article Journal of the Chemical Society, Perkin Transactions 1 · January 1, 1986 On oxidation with thallium(III) perchlorate in aqueous perchloric acid, methyl podocarpate (5) yielded two products which were identified on the basis of spectral data as the p-quinol (8) and the aryl ketone (7a) which resulted from oxidation at C-7 remote ... Full text Cite

Structure and stereochemistry of radermasinin, a novel cytotoxic triterpene lactone from Radermachia sinica. X-ray crystal structure of radermasinin monohydrate

Journal Article Journal of the Chemical Society, Chemical Communications · January 1, 1986 The structure and stereochemistry of radermasinin, a novel cytotoxic triterpene lactone isolated from Radermachia sinica, have been established from spectral data and single-crystal X-ray analysis of its monohydrate. ... Full text Cite

Boron Analogues of Choline. 2.1 Efficient Syntheses of Boron Analogues of Choline, Acetylcholine, and Substituted Acetylcholines

Journal Article Inorganic Chemistry · January 1, 1986 An efficient synthesis of isoelectronic and isostructural boron analogues of acetylcholine [CH3C(0)0CH2CH2N(Me2)BH3], benzoylcholine, (phenylacetyl)choline, and (phenoxyacetyl)choline from the reaction of the corresponding ester hydrochlorides with Et4NBH4 ... Full text Cite

Practical Conversion of Artemisinic Acid into Desoxyartemisinin

Journal Article Journal of Organic Chemistry · January 1, 1986 Artemisinin (Qinghaosu, 2) isolated from Artemisia annua has recently been used in China as a new type of antimalarial drug with rapid action and low toxicity against chloroquine-resistant malaria. Artemisinin is a novel sesquiterpene lactone bearing an un ... Full text Cite

Antineoplastic activity of a series of boron analogues of alpha-amino acids.

Journal Article Journal of pharmaceutical sciences · July 1985 A series of amine cyanoboranes, amine carboxyboranes, and boron analogues of alpha-amino acids have been investigated for antineoplastic activity against the growth of Ehrlich ascites cells. Additional studies demonstrated that the boron analogues inhibite ... Full text Cite

Identity of coleonol with forskolin: structure revision of a base-catalysed rearrangement product

Journal Article Tetrahedron Letters · January 1, 1985 The identity of coleonol and forskolin is shown through structure revision of a rearrangement product isolated earlier from coleonol and is confirmed by direct comparison of authentic coleonol with forskolin 1; in addition, coleonol-B should be correctly r ... Full text Cite

Isolation and structures of citropone-A and -B from citrus plants, first examples of naturally-occurring homoacridone alkaloids containing a tropone ring system

Journal Article Tetrahedron Letters · January 1, 1985 The first isolation of homoacridone alkaloids, citropone-A (1) and -B (2), from the root bark of Citrus grandis Osbeck f. buntan Hayata and C. natsudaidai Hayata is described. © 1985. ... Full text Cite

Thermal Transformation of Alkenoylated Aziridines into Ring-Fused Pyrrolidines

Journal Article Journal of Organic Chemistry · January 1, 1985 3-Phenyl- and 3-unsubstituted-2-alkenoyl-1-methylaziridines have been synthesized via Grignard reactions with the corresponding 2-cyanoaziridines. The 3-phenylated-2-alkenoylaziridines have been thermally transformed into ring-fused pyrrolidine compounds. ... Full text Cite

Hypolipidemic activity of tetrakis-mu-(trimethylamine-boranecarboxylato)-bis(trimethylamin e- carboxyborane)-dicopper(II) in rodents and its effect on lipid metabolism.

Journal Article Journal of pharmaceutical sciences · July 1984 A binuclear copper(II) complex was shown to have potent hypolipidemic activity in rats and mice at low doses, i.e., 2.5-10 mg/kg/d. The agent moderately lowered liver ATP-dependent citrate lyase, acetyl CoA synthetase, and phosphatidate phosphohydrolase ac ... Full text Cite

Antineoplastic activity of tetrakis-mu-(trimethylamine-boranecarboxylato)-bis (trimethylamine-carboxyborane)dicopper (II) in Ehrlich ascites carcinoma.

Journal Article Journal of pharmaceutical sciences · February 1984 A binuclear copper(II) complex derived from trimethylamine carboxyborane [tetrakis-mu-(trimethylamine-boranecarboxylato)-bis-(trimethyla mine- carboxyborane)dicopper(II)] was shown to have antineoplastic activity in the Ehrlich ascites carcinoma screen. Me ... Full text Cite

Structure and stereochemistry of maytensifolin-a, a novel hydroperoxy-nortriterpene from maytenus diversifolia

Journal Article Tetrahedron Letters · January 1, 1984 The structure and stereochemistry of the first hydroperoxy triterpene, maytensifolin-A, isolated from maytenus diversifolia, have been established from spectral and single-crystal X-ray analyses. © 1984. ... Full text Cite

Stereochemical assignments for the two enantiomeric pairs of 9,10-dihydroxy-Δ6a(10a)-Tetrahydrocannabinols. X-Ray Crystal Structure Analysis of (±)-Trans-Cannabitriol

Journal Article Journal of Natural Products · January 1, 1984 Single-crystal X-ray analysis of (±)-cannabitriol (1), isolated from Panamanian Cannabis, confirmed the structure of previously isolated (+)- and (-)-cannabitriol and defined the relative stereochemistry at the asymmetric centers. Based on the results obta ... Full text Cite

Structure of oxanthromicin (antibiotic 16–-550), a novel dimeric anthrone peroxide

Journal Article Journal of the Chemical Society - Series Chemical Communications · January 1, 1984 Oxanthromicin, an antibiotic isolated from an Actinomadura sp. SCC 1646 fermentation broth, has been assigned a novel dimeric peroxide structure based on chemical transformations and spectral data, and by a single-crystal X-ray analysis of a tetramethyl de ... Full text Cite

Structure and synthesis of physoperuvine: x-ray crystal and molecular structures of the n-benzoyl derivatives of (±)-3- and (+)-4-methylaminocycloheptanone

Journal Article Tetrahedron · January 1, 1984 Single-crystal X-ray analyses have defined the structures and solid-state conformations of (±)-N-benzoyl-3-methylaminocycloheptanone [(±)-3]and (+)-N-benzoyl-4-methylaminocycloheptanone [(±)4]. Resolution of (±)-[4- methylaminocycloheptanone α 1-hydroxytro ... Full text Cite

Synthesis of Sodium and Tetra-n-butylammonium Dicyanodihydroborates

Journal Article Inorganic Chemistry · January 1, 1984 Full text Cite

Studies in the Synthesis of C Ring Bridged Morphinans. 2.1 The Synthesis and Structural Verification of a Novel 3, llc-Ethano-10-hydroxy-6-methyl-l, 2, 3, 3a, llb, llc-hexahydroaporphine

Journal Article Journal of Organic Chemistry · January 1, 1984 The title compound and its 10-methoxy congener were prepared from bicyclo[2. 2. 2]oct-2-ene in approximately 2% overall yield. In the course of the synthesis of the final product, 14 novel bicyclo[2. 2. 2]-and-[3.2.1]octane derivatives were isolated and ch ... Full text Cite

Biologically Active Boron Analogs of α-Amino Acids and Derivatives

Journal Article Ventron Alembic · December 1983 Cite

Novel 17 alpha-chloro-17 beta-sulfinyl steroids as specific inhibitors of sebaceous gland activity: potential antiacne agents.

Journal Article Journal of medicinal chemistry · January 1983 The preparation and antisebaceous gland activities of a series of 17 alpha-chloro-17 beta-sulfinyl steroids are described. They were obtained from the corresponding 17 alpha-sulfides by chlorination and oxidation with iodobenzene dichloride in aqueous pyri ... Full text Cite

Biogenetic-type synthesis of santonin, chrysanolide, dihydrochrysanolide, tulirinol, arbusculin-C, tanacetin, and artemin

Journal Article Journal of the Chemical Society, Perkin Transactions 1 · January 1, 1983 The title compounds were synthesized from their possible biogenetic precursors through hydroperoxide intermediates generated by photo-oxygenation. This route for biological oxygenation may serve as a substitute to epoxidation. The 13C n.m.r. spectral assig ... Full text Cite

Serial Cyclization: Studies in the Mechanism and Stereochemistry of Peroxy Radical Cyclization

Journal Article Journal of the American Chemical Society · January 1, 1983 In this study two unsaturated hydroperoxides, model compounds for natural rubber, polyunsaturated isoprenoids such as polyprenols, and polybutadiene, were exposed to initiators in the presence of oxygen. The products of these reactions were isolated and fo ... Full text Cite

Stereochemically Complementary Reductions of Indoles

Journal Article Tetrahedron Letters · 1983 Cite

Kijanimicin. Part 3. Structure and absolute stereochemistry of kijanimicin

Journal Article Journal of the Chemical Society, Perkin Transactions 1 · January 1, 1983 Kijanimicin, a novel antibiotic from Actinomadura kijaniata nov. sp. SCC1256 (ATCC 31588), has been shown by chemical degradation, spectroscopic studies, and X-ray crystallographic studies to have a unique tetrpnic acid structure. The molecule contains a b ... Full text Cite

Direct Heterolysis of a Very Weak Carbon-Carbon Bond to a Carbocation and Carbanion

Journal Article Journal of the American Chemical Society · January 1, 1983 Full text Cite

Trans-reduction of 5-phenyl-1,2,3,4,5,6-hexahydroazepino[4,5-b]indole. X-ray crystallographic study of the geometry of an intermolecular N-H ⋯ phenyl hydrogen bond

Journal Article Journal of the Chemical Society, Perkin Transactions 2 · January 1, 1983 The stereochemistries of the two isomeric products (5) and (6) obtained in equal amounts from trans-reduction of 3-benzyl-5-phenyl-1,2,3,4,5,6- hexahydroazepino[4,5-b]indole (3) have been determined by spectral and single-crystal X-ray analyses. Monoclinic ... Full text Cite

The Structure of Callichiline

Journal Article Tetrahedron · 1983 Cite

Nitration of 2-alkoxytoluenes: formation of biphenyl derivatives

Journal Article The Journal of Organic Chemistry · August 1982 Full text Cite

Basicity and metal ion binding capability of amine-carboxyboranes, R3N·BH2COOH, boron analogs of glycine and N-methylated glycines

Journal Article Inorganica Chimica Acta · January 1, 1982 Ionization of the carboxylic acid proton from net zero charged amine-carboxyboranes, where amine = NH3, CH3NH2, (CH3)2NH, and (CH3)3N, occurs with pKa values of 8.33, 8.23, 8.14, and 8.38, respectively, at 0.5 M ionic strength and 21 °C. There is no eviden ... Full text Cite

Structure of protoveratrine C, a new alkaloid from provoveratrine

Journal Article Tetrahedron Letters · January 1, 1982 Single-crystal X-ray analysis has established that provoveratrine C, a third tetraester component of proveratrine, is protoverine 3-(2′S,3′R-2′,3′-dihydroxy-2′-methylbutyrate 6,7-diacetate 15-(2′R)-methylbutyrate. © 1982. ... Full text Cite

Synthesis and Conformational Properties of 3,8-Phosphonanedione 1-Oxides

Journal Article Journal of the American Chemical Society · January 1, 1982 Ozonolysis at −78 °C of 3-phospholene derivatives with cyclohexane or substituted cyclohexanes fused at the double bond provides a useful route to derivatives of the 3,8-phosphonanedione 1-oxide system. Synthesized were the 1-methyl, 1-phenyl, 1-hydroxy, 1 ... Full text Cite

Chemical degradation of AR-5 antibiotics (mycinamicins): X-ray crystal structure analysis of the aglycone from AR-5 #2

Journal Article Journal of the Chemical Society, Chemical Communications · January 1, 1982 The structures and stereochemistry of AR-5 antibiotics (mycinamicins) by X-ray analysis are disclosed; a novel degradative procedure for the preparation of the aglycones of the above antibiotics is also described. ... Full text Cite

Backbone rearrangements of methyl (-)-kaur-9(11)-en-19-oate and its epoxide: structures of two diterpenes of a new skeletal type

Journal Article Tetrahedron Letters · January 1, 1982 cleavage of the epoxide (2) of methyl (-)-kaur-9(11)-en-19-oate (1b) with boron trifluoride-ether in benzene and in acetic anhydride yielded (3a) and (3b), respectively. On epoxidation with m-chloroperbenzoic acid in the presence of N-nitrosomethyl urea, ( ... Full text Cite

Nuclear magnetic resonance and X-ray stereochemical studies on 1-benzyltetrahydroisoquinolinium salts

Journal Article Journal of the Chemical Society, Perkin Transactions 1 · January 1, 1982 The relative stereochemistry at positions 1 and 2 of N,N-dialkyl-1-benzyl- 1,2,3,4-tetrahydroisoquinolinium salts has been assigned via a combination of 1H and 13C n.m.r. studies and confirmed by single-crystal X-ray analysis of trans-N-3-hydroxypropyl-5′- ... Full text Cite

Structure and stereochemistry of maytenfolic acid and maytenfoliol, two new antileukemic triterpenes from maytenus diversifolia: X-ray crystal structures

Journal Article Journal of the Chemical Society, Chemical Communications · January 1, 1982 The structure and stereochemistry of maytenfolic acid and maytenfoliol, two new antileukemic triterpenes isolated from Maytenus diversifolia, have been established from chemical transformations and spectral and single-crystal X-ray analysis. ... Full text Cite

A Stereochemical Model of the Veratrum Alkaloids

Journal Article Journal of Organic Chemistry · January 1, 1982 A stereoselective synthesis beginning from the tetracyclic isoxazolidine 3 gave an inactive model (2) of rings D–F of the hypotensive Veratrum alkaloids (1). Cleaving, N-demethylating, and epimerizing 3 gave the amino alcohol 5a. Diazotizing 5a afforded la ... Full text Cite

X-ray crystal structure of rocaglamide, a novel antileukemic 1H-cyclopenta[b]benzofuran from Aglaia elliptifolia

Journal Article Journal of the Chemical Society, Chemical Communications · January 1, 1982 The structures and relative stereochemistries of rocaglamide, a novel antileukemic 1H-cyclopenta[b]benzofuran isolated from Aglaia elliptifolia, and dehydrorocaglamide, derived from rocaglamide, have been established from spectral and single-crystal X-ray ... Full text Cite

X-ray crystal structure determination and synthesis of the new isonitrile-containing antibiotics, hazimycin factors 5 and 6

Journal Article Journal of the Chemical Society, Chemical Communications · January 1, 1982 Two components of a new class of antibiotics, hazimycin factors 5 and 6, which are interconvertible in a base-catalysed process, are each shown to be di-tyrosine analogues containing two isonitrile groups; their synthesis by two routes, one of which involv ... Full text Cite

New Synthesis of Penems, the Oxalimide Cyclization Reaction

Journal Article Journal of the American Chemical Society · January 1, 1982 Full text Cite

Antihyperlipidemic activity of amine cyanoboranes, amine carboxyboranes, and related compounds.

Journal Article Journal of pharmaceutical sciences · March 1981 A series of amine cyanoboranes and amine carboxyboranes were observed to be antihyperlipidemic agents in mice; i.e., they lowered serum cholesterol and triglyceride levels significantly. These compounds appeared to inhibit lipid synthesis in the early stag ... Full text Cite

Carbocyclic analogs of C-nucleosides: a key intermediate via a novel and efficient CC ring scission

Journal Article Tetrahedron Letters · January 1, 1981 Treatment of hydroxymethylene ketone 6 with trimethylene dithiotosylate according to literature conditions,3b led to the novel CC ring scission product 7 in high yield; also, the hydroxide-initiated cleavage4 of 1 gave the β-elimination product 13 which un ... Full text Cite

Synthesis of racemic, 2-(alkylthio)-6-(1-hydroxyethyl) penems; attempted penem synthesis via copper (I) - promoted cyclisations

Journal Article Tetrahedron Letters · January 1, 1981 Stereocontrolled syntheses of the diastereoisomeric 6-(1-hydroxyethyl)-2-ethylthio and 2-(2-aminoethylthio)-penem-3-carboxylates from a common monocyclic azetidinone precursor are described. Cu (I)-promoted cyclisation of suitable N/C-3 secopenems is shown ... Full text Cite

Cycloaddition of vinyl aziridines with unsaturated substrates. A novel rearrangement of an unsaturated nitro compound.

Journal Article Tetrahedron Letters · January 1, 1981 Vinylaziridine 2 undergoes reaction with electrophilic acetylenes and olefins to produce 7-membered azepine derivatives. With β-nitro-styrene however, a novel rearrangement occurs, presumably via an ene reaction to form 10, the structure of which is defini ... Full text Cite

Phosphorus-Containing Cyclohexanes. Nuclear Magnetic Resonance Studies and Conformational Analysis of 1,3,2-Dithiaphosphorinanes

Journal Article Journal of the American Chemical Society · January 1, 1981 Proton, carbon-13, and phosphorus-31 NMR spectroscopic data were obtained for a variety of tricoordinate 1,3,2-dithiaphosphorinanes as well as tetracoordinate 2-oxo and 2-thiono derivatives. The tricoordinate compounds adopt a chair conformation in which a ... Full text Cite

Anti-inflammatory activity of amine cyanoboranes, amine carboxyboranes, and related compounds.

Journal Article Journal of pharmaceutical sciences · September 1980 Amine cyanoboranes and amine carboxyboranes (boron analogs of alpha-amino acids) were shown to inhibit inflammation. The analogs effectively blocked general inflammation, induced arthritis, and the writhing reflex associated with inflammation pain, while t ... Full text Cite

Anomalous behaviour of an allyl alcohol in reaction with iron pentacarbonyl

Journal Article Journal of Organometallic Chemistry · February 12, 1980 [(6,7,8,9-η)-Bicyclo[3.2.2]nona-2,6,8-trien-4-ol]tricabonyliron (6) rearranges in the presence of Fe(CO)5 to [(2,3,6,7-η)-bicyclo[3.2.2]nona-2,6,8-trien-4-one] tricarbonyliron (7); rather than [(6,7,8,9-η)-bicyclo-[3.2.2]nona-6,8-dien-2-one] tricarbonyliro ... Full text Cite

A Fixed-Geometry Study of the SH2 Reaction on the Peroxide Bond

Journal Article Journal of the American Chemical Society · January 1, 1980 Full text Cite

Conformation of epi-α-Cyperone and Related Enones

Journal Article Journal of Organic Chemistry · January 1, 1980 The conformations of epi-a-cyperone (10-epieudesma-4,ll-dien-3-one, 2) and its dihydro and 14-nor analogues (4 and 15, respectively) have been investigated by a combination of lanthanide induced shift reagent NMR, 13C NMR, and high-field NMR techniques. Co ... Full text Cite

Serial Cyclization of Peroxy Free Radicals: Models for Polyolefin Oxidation

Journal Article Journal of the American Chemical Society · January 1, 1980 Full text Cite

Structures of croverin (X-ray analysis) and dihydrocroverin, two new diterpene lactones from croton verreauxii baill

Journal Article Journal of the Chemical Society - Series Chemical Communications · January 1, 1980 The structures and stereochemistries of croverin and dihydrocroverin, two new diterpene lactones from Croton verreauxii Baill., have been elucidated by a combination of chemical, physical, and X-ray methods. © 1980, The Royal Society of Chemistry. All righ ... Full text Cite

Chemical Degradation and X-Ray Crystal Structure of Rosaramicin

Journal Article Tetrahedron Letters · 1980 Cite

X-Ray crystal and molecular structure of olgose, a major degradation product of the oligosaccharide antibiotic everninomicin D

Journal Article Journal of the Chemical Society, Chemical Communications · December 1, 1979 Single crystal X-ray analysis of olgose (4) unequivocally confirms all the structural features reported earlier and defines stereochemistry at C(4), (C6), and the orthoester carbon atom. ... Full text Cite

Crystal and molecular structure of diaquahydrogen(I) μ-oxo-[bis(diethyldithiocarbamato)oxomolybdate(IV)] [bis(diethyldithiocarbamato)oxomolybdenum(V)] bis{μ-oxo-bis[bis(diethyldithiocarbamato)oxomolybdenum(V)]} (1), and μ-oxo-bis[bis(diethyldithiocarbamato)oxomolybdenum(V)] (2), and the single-crystal electron spin resonance spectrum of (1)

Journal Article Journal of the Chemical Society, Dalton Transactions · December 1, 1979 Monoclinic crystals of form (1) belong to space group C2/c, with a = 31.340(10), b = 9.671(3),c = 38.027(10) Å, β = 110.72(5)°; the unit cell contains eight molecules of [MoO(S2CNEt2)2]2O oxo-bridged dimers (four with approximate C2 symmetry, four with cry ... Full text Cite

Plant antitumour agents-XV. Isolation and x-ray crystal structure of a new antileukaemic quassinoid undulatone from Hannoa undulata

Journal Article Tetrahedron · January 1, 1979 The structure of Undulatone, a new antileukaemic quassinoid from Hannoa undulata was determined by spectral means and confirmed by single crystal X-ray analysis of the methanol solvate. © 1979. ... Full text Cite

X-ray crystal structure analyses and conformational studies of cis-cyclo-octane-1,5-diol and cyclo-octane-1,5-dione

Journal Article Journal of the Chemical Society, Perkin Transactions 2 · January 1, 1979 Single-crystal X-ray analyses of cis-cyclo-octane-1,5-diol (1) and cyclo-octane-1,5-dione (2) have established that the eight membered rings in both compounds adopt boat-chair conformations in the solid state. The observed geometries accord well with those ... Full text Cite

3, 8-Thionanedione 1, 1-Dioxide. Synthesis and Solid-State Conformation

Journal Article Journal of Organic Chemistry · January 1, 1979 The title compound is conveniently prepared in 80% overall yield by ozonolysis at -78 °C of the cycloadduct of S02 with 1, 2-dimethylenecyclohexane. Single-crystal X-ray analysis establishes that the nine-membered ring adopts a twist-chair-chair conformati ... Full text Cite

X-Ray crystal structure of canellal, a novel antimicrobial sesquiterpene from Canella winterana

Journal Article Journal of the Chemical Society, Chemical Communications · December 1, 1978 Canellal (1), a novel antimicrobial sesquiterpene dialdehyde, has been isolated from the trunk bark of Canella winterana; its structure and stereochemistry were determined from spectral and single-crystal X-ray analyses. ... Full text Cite

Studies in eight-co-ordination. Part 5. Crystal and molecular structure and electron spin resonance spectra of tetrakis(diethyldithio-carbamato)molybdenum(V) hexamolybdate and chloride

Journal Article Journal of the Chemical Society, Dalton Transactions · December 1, 1978 The crystal structures of [Mo(S2CNEt2)4]2[Mo6O 19] (1) and [Mo(S2CNEt2)4]Cl (2) have been determined from diffractometer data by direct methods and refined by full-matrix least-squares calculations to R 0.050 and 0.083 over 2 893(1) and 3 079(2) statistica ... Full text Cite

Crystal and molecular structure and electron spin resonance spectrum of trichloro-oxobis(triphenylphosphine oxide)molybdenum(v)

Journal Article Journal of the Chemical Society, Dalton Transactions · December 1, 1978 Monoclinic crystals of the title complex belong to space group P21/c, and have unit-cell dimensions of a = 18.977(5), b = 16.860(5), c = 22.099(6) Å, β = 96.50(5), and Z = 8. The crystal structure has been solved by direct methods using 3 286 statistically ... Full text Cite

Synthesis, structure, and acetolysis of some fused cyclobutane derivatives

Journal Article Journal of the American Chemical Society · April 1978 Full text Cite

SYNTHESIS AND X-RAY CRYSTAL-STRUCTURE CHARACTERIZATION OF AMMONIA-CYANOBORANE

Journal Article JOURNAL OF CHEMICAL RESEARCH-S · 1978 Cite

Mechanism of Olefin Rearrangements Induced by Iron Carbonyls. Rearrangements in the Bicyclo[6.1.0]nonene System

Journal Article Inorganic Chemistry · January 1, 1978 9,9-Dichlorobicyclo[6.1.0]non-4-ene (28) rearranged to the bicyclonon-3-ene isomer 29 and ultimately to bicyclonon-2-ene (30) in the presence of Fe2(CO)9. The tetracarbonyliron(0) complex of the bicyclonon-3-ene isomer (33) was isolated and subjected to si ... Full text Cite

X-Ray crystal and molecular structure of channaine, an unusual alkaloid, probably an artefact from Sceletium strictum

Journal Article Journal of the Chemical Society, Chemical Communications · January 1, 1978 The structure of channaine (3), derived by spectral and single-crystal X-ray analyses, indicates that this alkaloid is probably an artefact which arises from the condensation of a pair of N-demethylmesembrenone (4) molecules during the isolation process. ... Full text Cite

Structure of the compound purported to be NN-bis(chloromethyldimethylsilyl) -acetamide: X-ray crystal structure analysis of the novel five-membered oxygen-, silicon-, and nitrogen-containing heterocycle (O-Si)-chloro-[(N- chlorodimethylsilylacetamido)methyl]dimethylsilane

Journal Article Journal of the Chemical Society, Chemical Communications · January 1, 1978 The compound erroneously reported as NN-bis(chloromethyldimethylsilyl) acetamide has been proven by single-crystal X-ray analysis to be (O-Si)-chloro-[(N-chlorodimethylsilylacetamido)methyl]dimethylsilane. ... Full text Cite

Stereochemistry at C-3 of evernitrose: A fallacy in the determination of stereochemistry at quaternary centres using nuclear magnetic resonance spectroscopy. X-Ray crystal structure of methyl 3-acetamido-2,3,6-trideoxy-3-c, 4-O-dimethyl-L-xylo-hexopyranoside

Journal Article Journal of the Chemical Society, Chemical Communications · December 1, 1977 Single crystal X-ray analysis of the title compound (8) is reported which establishes the stereochemistry at C-3 of evernitrose. ... Full text Cite

Crystal and molecular structure, electron spin resonance, and electronic spectrum of tetraphenylarsonium tetrachloro-oxomolybdenum(V)

Journal Article Journal of the Chemical Society, Dalton Transactions · December 1, 1977 Crystals of the title compound are tetragonal, space group P4/n, with a = 12.766(7), c = 7.785(5) Å, Z = 2. The crystal structure was solved by the heavy-atom method and refined by full-matrix least-squares calculations to R 0.050 over 735 statistically si ... Full text Cite

Synthesis of Δ11-9α-fluoro-steroids: X-ray crystal and molecular structure of 17α,21-dipropionyloxy-9α-fluoro-16β- methylpregna-1,4,11-triene-3,20-dione

Journal Article Journal of the Chemical Society, Chemical Communications · December 1, 1977 Reaction of 9α-fluoro-corticosteroids with NN-dialkylaminosulphur trifluorides gives Δ11-9α-fluoro-steroids (2a,b); a single-crystal X-ray analysis of (2a) is reported. ... Full text Cite

Conformational preference of ring A in 3-oxo-∆5,10-steroids : X-ray crystal structure analysis of 17α-ethynyl-17β-hydroxyestr-5(10)-en-3-one (norethynodrel)

Journal Article Journal of the Chemical Society, Perkin Transactions 2 · January 1, 1977 The crystal structure and solid-state conformations of the title compound (5) have been established by X-ray analysis. Crystals are orthorhombic, space group P212121, with a= 21.593(13), b= 22.075(13), c= 7.015(8)Å, Z= 8. The structure was solved by direct ... Full text Cite

The Structure of Annonalide

Journal Article Tetrahedron Letters · 1977 Cite

Synthesis, crystal and molecular structure of a 1,11-etheno-steroid: 3-methyoxy-1,11-ethenoestra-1,3,5(10),9(11)-tetraen-17-one.

Journal Article Journal of the Chemical Society. Perkin transactions 1 · January 1977 Cite

X-ray structural and conformational analyses of the erythrina alkaloids cocculine and coccutrine

Journal Article Journal of the Chemical Society, Perkin Transactions 2 · January 1, 1977 Crystal structures of the title alkaloids have been established by direct phase-determining methods and atomic parameters refined by full-matrix least-squares calculations to R 0.063 (1) and 0.078 (2) over 960 (1) and 1 342 (2) reflections from diffractome ... Full text Cite

Synthesis of 6β,7β-Nitromethylene Steroids

Journal Article Tetrahedron Letters · 1977 Cite

Synthesis and Characterization of 1,2-Nitromethylene Steroids

Journal Article Tetrahedron Letters · 1977 Cite

Crystal and molecular structure, electron spin resonance, and electronic spectrum of tetrakis(imidazole)dinitratocopper(II)

Journal Article Journal of the Chemical Society, Dalton Transactions · December 1, 1976 The structure of the title compound has been established by single-crystal X-ray analysis. Crystals are orthorhombic, space group Pna21, a = 13.85(1), b = 9.83(1), c = 13.39(1) Å, Z = 4. The structure was solved by the heavy-atom method and atomic paramter ... Full text Cite

Structure and stereochemistry of microlenin, a novel antitumour dimeric sesquiterpene lactone from Helenium microcephalum; X-ray crystal structure

Journal Article Journal of the Chemical Society, Chemical Communications · December 1, 1976 The structure and stereochemistry of microlenin, a novel antitumour sesquiterpene lactone isolated from Helenium microcephalum, have been established from spectral and single-crystal X-ray analyses. ... Full text Cite

Synthesis, crystal and molecular structure of a stable monomeric five-co-ordinate gallium-amine complex, chloro(dimethyl)-1, 10-phenanthrolinegallium(III)

Journal Article Journal of the Chemical Society, Dalton Transactions · December 1, 1976 X-Ray single-crystal analysis, lH n.m.r., and molecular-weight measurements establish that the title compound has a trigonal bipyramidal structure in the solid state and in chloroform, but ionizes in water. Crystals are monoclinic, space group P21/c, with ... Full text Cite

Formation of an unusual steroidal oxetane and its transformation products.

Journal Article The Journal of organic chemistry · December 1976 Full text Cite

Stereoselective β-face catalytic hydrogenation of Δ4- 9α-fluoro-11β-hydroxycorticosteroids: Reappraisal

Journal Article Journal of the Chemical Society, Chemical Communications · December 1, 1976 At variance with previous reports, palladium-catalysed reduction of 9α-fluorohydrocortisone 21-acetate (1a) and 1,2-didehydro-9α-fluoro- 16α-methylhydrocortisone 21-acetate (2a) yields the 5β-configuration. ... Full text Cite

N-Aryl-S,S-dimethyliminosulfuranes. Structure, Dipole Moments, and Extent of Double Bonding

Journal Article Journal of Organic Chemistry · June 1, 1976 The crystal structure of N-(p-nitrophenyl)-S,S-dimethyliminosulfurane is reported. The short N-S bond (1.651 Å) implies a substantial amount of double bonding and bond length distortions in the aromatic ring suggest extensive resonance involvement of the p ... Full text Cite

Crystal and molecular structure of carolenalone, a cycloheptenone sesquiterpene lactone from north carolina Helenium autumnale L

Journal Article Journal of the Chemical Society, Perkin Transactions 2 · January 1, 1976 X-Ray single crystal analysis has established the structure and relative stereochemistry of the title compound (I). Crystals are orthorhombic, space group P212121, a = 7.31 (1), b = 21.20(1), c = 9.21 (1) Å, Z = 4. The stru ... Full text Cite

Crystal and molecular structure of eupaformonin, a cytotoxic germacranolide from Eupatorium formosanum HAY

Journal Article Journal of the Chemical Society, Perkin Transactions 2 · January 1, 1976 Single-crystal X-ray analysis has established the structure and relative stereochemistry of the title compound (I). The absolute configuration follows from the sign of the Cotton effect of the n-→π* transition of the α-methylene γ-lactone C=C-C=O chromopho ... Full text Cite

X-ray crystal structure conformational studies on r-4,c-6-dimethyl-1,3- dithian and its oxides, r-4,c-6-dimethyl-1,3-dithian t-1-oxide, and r-4,c-6-dimethyl-1,3-dithian t-1,t-3-dioxide

Journal Article Journal of the Chemical Society, Perkin Transactions 2 · January 1, 1976 The crystal structures of the title compounds [the 1,3-dithian (I), and its oxides (II) and (III)] have been determined from X-ray diffractometer data. Monoclinic crystals of (I) and (II) are isomorphous, space group C2/c. with for (I) : a = 20.08(1), b = ... Full text Cite

Structures and conformations of the fourteen-membered ring diterpene ovatodiolide and its acid cyclization product: Nuclear overhauser effect studies in solution and X-ray crystal structure analyses of ovatodiolide and ovatodiolic acid

Journal Article Journal of the Chemical Society, Perkin Transactions 2 · January 1, 1976 The conformation and relative stereochemistry of ovatodiolide (1), a fourteen-membered ring diterpene dilactone isolated from Anisomeles ovata, have been elucidated by 1H n.m.r. spectroscopy including intramolecular nuclear Overhauser effect mea ... Full text Cite

X-ray crystal structure characterization of cyclo(hexacyanoborane), (BH2CN)6

Journal Article Journal of the Chemical Society, Dalton Transactions · December 1, 1975 The geometry of the title compound has been established by single-crystal X-ray analysis. Crystals are triclinic, space group P1, with a = 10.01(1), b = 8.78(1) c = 4.90(1) Å, α = 110.2(1), β = 93.9(1), γ = 70.5(1)°, Z = 1. The structure was solved by dire ... Full text Cite

Crystal and molecular structures of dinitrato(1,10-phenanthroline)copper(II) and diaquanitrato(1,10-phenanthroline)copper(II) nitrate

Journal Article Journal of the Chemical Society, Dalton Transactions · December 1, 1975 The crystal structures of the title compounds, (I) [Cu(C12H8N2)(NO3)2] and (II) [Cu(C12H8N2)(NO3)(H 2O)2]-[NO3], have been determined from three-dimensional X-ray diffractometer data and refined by full-matrix least-squares calculations to R 0.045 [(I), 1 ... Full text Cite

Crystal and molecular structure, electron spin resonance, and electronic spectrum of hexakis(imidazole)copper(II) nitrate

Journal Article Journal of the Chemical Society, Dalton Transactions · January 1, 1975 The structure of the title compound has been established by three-dimensional X-ray crystal-structure analysis from diffractometer data. Crystals are monoclinic, space group P21/c, with a = 8.65(1), b = 17.64(1), c = 8.38(1) Å, β = 93.20(10)°, Z ... Full text Cite

Structure and absolute configuration of florilenalin: X-ray analysis of 4-O-acetyl-2-O-p-iodobenzoylflorilenalin

Journal Article Journal of the Chemical Society, Perkin Transactions 2 · January 1, 1975 X-Ray single-crystal analysis has established the structure and absolute configuration of (IV), the 4-O-acetyl-2-O-p-iodobenzoyl derivative of florilenalin (II), a cytotoxic guaianolide from Helenium automnale L. Crystals are orthorhombic, space group P2 Full text Cite

Structure and absolute configuration of plenolin: X-ray analysis of plenolin p-iodobenzoate

Journal Article Journal of the Chemical Society, Perkin Transactions 2 · January 1, 1975 The structure and absolute configuration of the cytotoxic pseudoguaianolide sesquiterpene lactone, plenolin (II), have been determined by X-ray analysis of the p-iodobenzoate derivative (III). Crystals of (III) are orthorhombic, space group P212 ... Full text Cite

X-ray determination of the structure and conformation of an oxide from helenalin

Journal Article Journal of the Chemical Society, Perkin Transactions 2 · January 1, 1975 The crystal and molecular structure of the oxide (II) produced by the reaction of helenalin (I) with hydrogen chloride-chloroform and deactivated neutral alumina has been established by X-ray analysis from photographic data. Crystals are orthorhombic, spac ... Full text Cite

Crystal structure and conformation of 17α-ethynyl-17β-hydroxy-6,6-dimethyl-6-sila-5α-estr-1(10)-en-3- one

Journal Article Journal of the Chemical Society, Perkin Transactions 2 · January 1, 1975 The crystal and molecular structure of the title compound (I) has been established by X-ray analysis. Crystals are monoclinic, space group P21/c, with a = 12.87(2), b = 6.61(1), c = 23.32(3) Å, β = 97.87(10)°, Z = 4. The structure was solved by ... Full text Cite

Structure and Absolute Stereochemistry of Dihydroflorilenalin, A New Sesquiterpene Lactone from Florida Helenium autumnale L.

Journal Article Chemical and Pharmaceutical Bulletin · January 1, 1975 The structure and absolute stereochemistry of dihydroflorilenalin, a new guaianolide isolated from Helenium autumnale L., have been determined on the basis of physicochemical data, chemical transformation, and X-ray crystallographic analysis. © 1975, The P ... Full text Cite

Crystal and molecular structure of eupatolide, the major cytotoxic principle from Eupatorium formosanum HAY

Journal Article Journal of the Chemical Society, Perkin Transactions 2 · January 1, 1975 Single-crystal X-ray analysis of eupatolide [8β-hydroxygermacra-1 (10),4,11(13)-trien-12,6α-olactone] has established the detailed molecular conformation and the absolute configuration follows from the known sign of the Cotton effect of the n→π* transition ... Full text Cite

The Conformational Equilibrium in S-Methylthianium Perchlorate

Journal Article J. Amer. Chem. Soc. · 1974 Cite

Preparation and X-ray crystal structure of a novel tetranuclear copper(I) ethylenethiourea cluster complex, μ4-ethylenethiourea-cyclo- tetrakis-μ-(ethylenethiourea)tetrakis[ethylenethioureacopper(I)] nitrate hexahydrate

Journal Article Journal of the Chemical Society, Chemical Communications · January 1, 1974 The structure, geometry, and bonding in [Cu4(C3H 6N2S)9(NO3)4],6H 2O have been established by X-ray analysis which reveals discrete Cu4(C3H6N2S)94+ cations containing an alternating Cu-S eight-membered ring with a unique ethylenethiourea ligand in an axial ... Full text Cite

Isolation and characterization of chloro(ethyl) dimethylglyoximatodimethylglyoximecobalt(III) hydrate. A protonated cobaloxime

Journal Article Journal of the Chemical Society, Chemical Communications · December 1, 1973 A monoprotonated cobaloxime, [EtCo(dmg)(dmgH)Cl]H2O, has been isolated and characterized by i.r., u.v., and X-ray methods which indicate a dimethylglyoxime oxygen as the site of protonation. ... Full text Cite

Crystal and Molecular Structure of Mesembranol

Journal Article J. Chem. Soc. Perkin II · 1973 Cite

Stereoselectivity Due to Electrostatic Repulsion in Polar Cycloadditions

Journal Article J. Chem. Soc. Chem. Commun. · 1973 Cite

X-Ray Crystal Structure Revision for the Frugal Metaolite (&#177)-Altenuene

Journal Article J. Chem. Soc. Chem. Commun. · 1973 Cite

Conformations of D-Norsteroids by X-Ray Analysis

Journal Article Chem. Commun. · 1971 Cite

The Conformation of Ring C in 8-Podocarpenes

Journal Article Tetrahedron Letters · 1971 Cite

The Friedel-Crafts Reaction with 5-Arylidene-4-thiazolidinones

Journal Article International J. of Sulfur Chem. · 1971 Cite

Molecular Structure of 1-Benzylphosphole by X-Ray Analysis

Journal Article J. Amer. Chem. Soc. · 1970 Cite

Conformation of Xylocholine

Journal Article Nature · 1969 Cite

Configurations of Arene-Chromium Tricarbonyls

Journal Article Chem. Commun. · 1966 Cite

Hydroxyl-Benzene Hydrogen Bonding: an X-Ray Study

Journal Article Chem. Commun. · 1965 Cite

The Stereochemistry of Acorone

Journal Article Chem. Commun. · 1965 Cite

Stereochemistry of Humulene

Journal Article Chem. and Ind. · 1964 Cite

The Constitution and Absolute Stereochemistry of Swietenine

Journal Article Tetrahedrom Letters · 1964 Cite

The Structure of Ergoflavin

Journal Article Proc. Chem. Soc. · 1963 Cite

Alkaloids of Calabash Curare: The Structure of Macusine-A

Journal Article Proc. Chem. Soc. · 1961 Cite

The Structure of Carcurine-II

Journal Article Proc. Chem. Soc. · 1961 Cite

The Structure of Acetyl-bromogeigerin

Journal Article Proc. Chem. Soc. · 1960 Cite