Steven W. Baldwin
Professor of Chemistry
The central themes of our research program are the development of methodology to accomplish the synthesis of optically pure materials and the subsequent application of the new methodology to the total synthesis of biologically significant natural products.
At the present time there are several different approaches to a variety of targets in progress in our laboratories. The first is the transfer of chirality from optically active hydroxylamines (e.g.,1) employing intra-and intermolecular nitrone /alkene cycloaddition reactions in the chirality transfer step. Particular targets for this chemistry are several ''unusual'' alpha-amino acids (2) as well as alkaloids related to pretazettine (3). The synthesis of pretazettine is also being addressed in a different approach involving a chiral ring expansion of allylic alcohol (4).
Recently, significant progress has been realized in the synthesis the alkaloid gelsemicine (7) based on the Diels-Alder reaction of chiral maleimides such as (5). It has been found, for instance, that diastereomeric ratios in excess of 50/1 can be realized when (5) is allowed to react with silicon substituted butadiene (6) in a Lewis-acid catalyzed reaction.
Current Appointments & Affiliations
- Professor of Chemistry, Chemistry, Trinity College of Arts & Sciences 1987
Contact Information
- 1101 French Science Center, Durham, NC 27708
- Box 90346, Durham, NC 27708-0346
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steven.baldwin@duke.edu
(919) 660-1563
- Background
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Education, Training, & Certifications
- Ph.D., California Institute of Technology 1969
- B.A., Dartmouth College 1964
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Previous Appointments & Affiliations
- Director of Graduate Studies in the Department of Chemistry, Chemistry, Trinity College of Arts & Sciences 2008 - 2011
- Chair, Chemistry, Trinity College of Arts & Sciences 1995 - 1999
- Adjunct Professor, Education, Trinity College of Arts & Sciences 1989 - 1992
- Director, Graduate Studies (MAT), Chemistry, Trinity College of Arts & Sciences 1989 - 1991
- Associate Professor with Tenure, Chemistry, Trinity College of Arts & Sciences 1976 - 1987
- Assistant Professor, Chemistry, Trinity College of Arts & Sciences 1970 - 1976
- Research
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Selected Grants
- Research Experiences for Undergraduates in Chemistry awarded by National Science Foundation 1997 - 2000
- Strategies for Tetrodotoxin and Azadirachtin awarded by National Institutes of Health 1994 - 1998
- Undergraduate Research Experiences in Chemistry at Duke University awarded by National Science Foundation 1997 - 1998
- Research Experiences for Undergraduates in Chemistry at Duke University awarded by National Science Foundation 1994 - 1997
- New Methodology for Glycoproteins awarded by National Institutes of Health 1992 - 1997
- Research Experiences for Undergraduates in Chemistry at Duke University awarded by National Science Foundation 1994 - 1996
- A 400 MHZ NMR Spectrometer for Chemical Research awarded by National Science Foundation 1995 - 1996
- NSF Minority Fellowship awarded by National Science Foundation 1995 - 1996
- Undergraduate Research Experiences in Chemistry at Duke University awarded by National Science Foundation 1994 - 1995
- Synthesis of Some Optically Active Geisemium Alkaloids awarded by National Institutes of Health 1993 - 1995
- Publications & Artistic Works
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Selected Publications
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Academic Articles
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Baldwin, S. M., J. E. Bercaw, L. M. Henling, M. W. Day, and H. H. Brintzinger. “Cationic alkylaluminum-complexed zirconocene hydrides: NMR-spectroscopic identification, crystallographic structure determination, and interconversion with other zirconocene cations.” Journal of the American Chemical Society 133, no. 6 (2011): 1805–13. https://doi.org/10.1021/ja1050428.Full Text
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Baldwin, S. M., J. E. Bercaw, and H. H. Brintzinger. “Cationic alkylaluminum-complexed zirconocene hydrides as participants in olefin polymerization catalysis.” Journal of the American Chemical Society 132, no. 40 (October 13, 2010): 13969–71. https://doi.org/10.1021/ja105040r.Full Text
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Adler, M. J., and S. W. Baldwin. “Direct, regioselective synthesis of 2,2-dimethyl-2H-chromenes. Total syntheses of octandrenolone and precocenes I and II.” Tetrahedron Letters 50, no. 36 (September 9, 2009): 5075–79. https://doi.org/10.1016/j.tetlet.2009.06.090.Full Text
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Baldwin, S. M., J. E. Bereaw, and H. H. Brintzinger. “Alkylaluminum-complexed zirconocene hydrides: Identification of hydride-bridged species by NMR spectroscopy.” Journal of the American Chemical Society 130, no. 51 (December 24, 2008): 17423–33. https://doi.org/10.1021/ja8054723.Full Text
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Mao, Zhan, and Steven W. Baldwin. “New spirocyclic oxindole synthesis based on a hetero Claisen rearrangement.” Organic Letters 6, no. 14 (July 2004): 2425–28. https://doi.org/10.1021/ol0491888.Full Text
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Baldwin, Steven W., and Alan Long. “2-tert-butyl-3-methyl-2,3-dihydroimidazol- 4-one-N-oxide: a new nitrone-based chiral glycine equivalent.” Organic Letters 6, no. 10 (May 2004): 1653–56. https://doi.org/10.1021/ol049505a.Full Text
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DeGrado, T. R., S. W. Baldwin, S. Wang, M. D. Orr, R. P. Liao, H. S. Friedman, R. Reiman, D. T. Price, and R. E. Coleman. “Synthesis and evaluation of (18)F-labeled choline analogs as oncologic PET tracers.” J Nucl Med 42, no. 12 (December 2001): 1805–14.Link to Item
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Long, A., and S. W. Baldwin. “Enantioselective syntheses of homophenylalanine derivatives via nitrone 1,3-dipolar cycloaddition reactions with styrenes.” Tetrahedron Letters 42, no. 32 (August 6, 2001): 5343–45. https://doi.org/10.1016/S0040-4039(01)00821-8.Full Text
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DeGrado, T. R., R. E. Coleman, S. Wang, S. W. Baldwin, M. D. Orr, H. S. Friedman, C. Robertson, and D. T. Price. “Synthesis and Evaluation of 18F-labeled Choline as an Oncologic PET Tracer.” Cancer Research 61 (2001): 110–17.
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DeGrado, T. R., R. E. Coleman, S. Wang, S. W. Baldwin, M. D. Orr, C. N. Robertson, T. J. Polascik, and D. T. Price. “Synthesis and evaluation of 18F-labeled choline as an oncologic tracer for positron emission tomography: initial findings in prostate cancer.” Cancer Res 61, no. 1 (January 1, 2001): 110–17.Link to Item
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Coleman, R., T. DeGrado, S. Wang, S. Baldwin, M. Orr, R. Reiman, and D. Price. “9:30-9:45. Preliminary Evaluation of F-18 Fluorocholine (FCH) as a PET Tumor Imaging Agent.” Clin Positron Imaging 3, no. 4 (July 2000): 147. https://doi.org/10.1016/s1095-0397(00)00059-5.Full Text Link to Item
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Baldwin, S. W., P. Chen, N. Nikolic, and D. C. Weinseimer. “A solution to the cyclic aldol problem.” Organic Letters 2, no. 9 (May 2000): 1193–96. https://doi.org/10.1021/ol005525a.Full Text
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Baldwin, S. W., and J. Debenham. “Stereospecific Total Syntheses of Optically Pure (-)-Haemanthidine, (+)-Pretazettine, and (+)-Tazettine.” Org. Lett. 2 (2000): 99.
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Baldwin, S. W., and J. S. Debenham. “Total syntheses of (-)-haemanthidine, (+)-pretazettine, and (+)-tazettine.” Organic Letters 2, no. 2 (January 2000): 99–102. https://doi.org/10.1021/ol9911472.Full Text
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Pullen, S. H., S. L. Martinez, A. L. Harris, A. Long, S. W. Baldwin, H. A. Staab, and J. D. Simon. “Comparison of the Photoinduced Electron Transfer Reaction in a Rigid Cyclophane with its Corresponding Bimolecular Donor/Acceptor Complex.” J. Phys. Chem. A. 103 (1999): 10220.
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Baldwin, S. W., B. G. Young, and A. T. McPhail. “Preparation and evaluation of a cyclic acyl nitrone as a synthon for stereospecific α-amino acid synthesis.” Tetrahedron Letters 39, no. 38 (September 17, 1998): 6819–22. https://doi.org/10.1016/S0040-4039(98)01474-9.Full Text
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Baldwin, S. W., A. T. McPhail, and J. Aubé. “Studies Directed at the Synthesis of Optically Active Pretazettine via Intramolecular Nitrone/Alkene Cycloaddition Reactions.” Journal of Organic Chemistry 56, no. 23 (November 1, 1991): 6546–50. https://doi.org/10.1021/jo00023a019.Full Text
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Baldwin, S. W., P. Greenspan, C. Alaimo, and A. T. McPhail. “Diastereoselective diels-alder reactions between substituted 1,3-butadienes and n-α-methylbenzylmaleimide.” Tetrahedron Letters 32, no. 42 (October 14, 1991): 5877–80. https://doi.org/10.1016/S0040-4039(00)79415-9.Full Text
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Baldwin, S. W., and J. M. McIver. “Stereochemistry of the reactions of some "CH3-" nucleophiles with 2-(tetrahydrofur-2′-yl)-acetaldehyde.” Tetrahedron Letters 32, no. 17 (April 22, 1991): 1937–40. https://doi.org/10.1016/0040-4039(91)85006-Q.Full Text
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Baldwin, S. W., and S. C. Gedon. “Effect of Nitrogen Substitution on the Diastereoselection of Intramolecular Nitrone/Alkene Cycloadditions.” Synthetic Communications 21, no. 4 (February 1, 1991): 587–96. https://doi.org/10.1080/00397919108016788.Full Text
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Baldwin, S. W., and J. M. McIver. “Nucleophiles with 2-(Tetrahydrofur-2'-γl)-Acetaldehyde.” Tetrahedron Lett. 32, no. 17 (1991): 1937.
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Baldwin, S. W., and S. C. Gedon. “Effect of Nitrogen Substitution on the Diastereoselection of Intramolecular Nitrone/Alkene Cycloadditions.” Syn. Commun. 41, no. 4 (1991): 587.
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Aub, SW Baldwin RB McFadyen J., SW Baldwin RB McFadyen J. 233, and J. D. Wilson. “Diastereoselectivity in the Intramolecular Cycloaddition Reactions of Nitrones Derived from 5-Alkenals and Chiral Hydroxylamines.” Tetrahedron Lett. 32 (1991): 4431.
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Baldwin, S. W., and J. Aubé. “Asymmetric synthesis with chiral hydroxylamines. Synthesis of optically pure 4-substituted azetidinones.” Tetrahedron Letters 28, no. 2 (January 1, 1987): 179–82. https://doi.org/10.1016/S0040-4039(00)95680-6.Full Text
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Baldwin, S. W., and J. M. Mclver. “Stereoselective Synthesis of (±)-methyl Nonactate.” Journal of Organic Chemistry 52, no. 2 (January 1, 1987): 320–22. https://doi.org/10.1021/jo00378a043.Full Text
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Baldwin, S. W., T. J. Mazzuckelli, and P. M. Gross. “Face selectivity in the [2+2] photoannelation of chiral 3(2h)-furanones with alkenes.” Tetrahedron Letters 27, no. 49 (January 1, 1986): 5975–78. https://doi.org/10.1016/S0040-4039(00)85376-9.Full Text
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Baldwin, S. W., G. F. Martin, and D. S. Nunn. “Total Synthesis of (+)-Elemol by Photoannelation.” Journal of Organic Chemistry 50, no. 26 (January 1, 1985): 5720–23. https://doi.org/10.1021/jo00350a055.Full Text
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Wilson, SW Baldwin J. D., J. Aub, and J. 233. “Regiochemistry in the Intramolecular Cycloadditions of Substituted 5-Alkenyl Nitrones.” J. Org. Chem. 50 (1985): 4432.
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Baldwin, S. W., and H. R. Blomquist. “Facile synthesis of 2-substituted cyclopentenones.” Tetrahedron Letters 23, no. 38 (January 1, 1982): 3883–86. https://doi.org/10.1016/S0040-4039(00)87733-3.Full Text
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Baldwin, S. W., and H. R. Blomquist. “Cyclohexenones by the Barton Fragmentation of Tertiary Alcohols Derived from Furanone/Alkene Photoadducts.” Journal of the American Chemical Society 104, no. 18 (January 1, 1982): 4990–92. https://doi.org/10.1021/ja00382a061.Full Text
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Baldwin, S. W., and J. E. Fredericks. “Spiro[4.5]decanes by photoannelation. Total synthesis of (-)-acorenone.” Tetrahedron Letters 23, no. 12 (January 1, 1982): 1235–38. https://doi.org/10.1016/S0040-4039(00)87069-0.Full Text
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Baldwin, S. W., and M. T. Crimmins. “Total Synthesis of (−)-Sarracenin by Photoannelation.” Journal of the American Chemical Society 104, no. 4 (January 1, 1982): 1132–34. https://doi.org/10.1021/ja00368a054.Full Text
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Baldwin, S. W., and N. G. Landmesser. “Total synthesis of d,1-occidentalol by photoannelation.” Tetrahedron Letters 23, no. 43 (January 1, 1982): 4443–46. https://doi.org/10.1016/S0040-4039(00)85623-3.Full Text
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Baldwin, S. W. “Synthetic Aspects of [2 + 2] Cycloadditions of α,ß-Unsaturated Carbonyl Compounds.” Organic Photochemistry 5 (1981).
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Baldwin, S. W., and J. C. Tomesch. “Total Synthesis of dl-Cyclosativene by Cationic Olefinic and Acetylenic Cyclizations.” Journal of Organic Chemistry 45, no. 8 (January 1, 1980): 1455–62. https://doi.org/10.1021/jo01296a022.Full Text
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Baldwin, S. W., and J. M. Wilkinson. “Four-Carbon Photochemical Annelation of Alkenes with 2,2,6-Trimethyl-1,3-dioxolenone.” Journal of the American Chemical Society 102, no. 10 (January 1, 1980): 3634–35. https://doi.org/10.1021/ja00530a059.Full Text
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Baldwin, S. W., and T. Crimmins. “Synthesis of the Alleged Genipic Acid by Photoannelation.” Journal of the American Chemical Society 102, no. 3 (January 1, 1980): 1198–1200. https://doi.org/10.1021/ja00523a064.Full Text
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Baldwin, S. W., and J. M. Wilkinson. “Cyclohexenones by the photoannelation of alkenes with 2,2-dimethyl-3(2H)-furanone.” Tetrahedron Letters 20, no. 29 (January 1, 1979): 2657–60. https://doi.org/10.1016/S0040-4039(01)86378-4.Full Text
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Baldwin, S. W., and R. J. Doll. “Synthesis of the 2-aza-7-oxatricyclo[4.3.2.04,8]undecane nucleus of some gelsemium alkaloids.” Tetrahedron Letters 20, no. 35 (January 1, 1979): 3275–78. https://doi.org/10.1016/S0040-4039(01)95383-3.Full Text
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Baldwin, S. W., M. T. Crimmins, and V. I. Cheek. “A convenient preparation of α-methylene-d-valerolactones.” Synthesis (Germany) 1978, no. 3 (March 1, 1978): 210–11. https://doi.org/10.1055/s-1978-24708.Full Text
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Baldwin, S. W., M. T. Crimmins, and P. M. Gross. “A facile synthesis of δ-valerolactones by photoannelation.” Tetrahedron Letters 19, no. 44 (January 1, 1978): 4197–4200. https://doi.org/10.1016/S0040-4039(01)95180-9.Full Text
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Baldwin, S. W., and N. G. Landmesser. “Benzyl and Allyl Diazoacetate in One Carbon Ring Expansions of Ketones.” Synthetic Communications 8, no. 6 (January 1, 1978): 413–19. https://doi.org/10.1080/00397917808063567.Full Text
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Baldwin, S. W., P. W. Jeffs, and S. Natarajan. “Preparation of Norcocaine.” Synthetic Communications 7, no. 1 (January 1, 1977): 79–84. https://doi.org/10.1080/00397917709410059.Full Text
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Baldwin, S. W., and T. H. O’Neill. “Benzylic Bromination With Bromotrichloromethane.” Synthetic Communications 6, no. 2 (January 1, 1976): 109–12. https://doi.org/10.1080/00397917608072618.Full Text
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Baldwin, S. W., and S. A. Haut. “Reductive Deoxygenation of Esters with Trichlorosilane.” Journal of Organic Chemistry 40, no. 26 (December 1, 1975): 3885–87. https://doi.org/10.1021/jo00914a016.Full Text
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Baldwin, S. W., R. E. Gawley, R. J. Doll, and K. H. Leung. “Photoannelations with α-Formyl Ketones. Enol Specificity in the Reaction of Acyclic α-Formyl Ketones with Alkenes.” Journal of Organic Chemistry 40, no. 12 (June 1, 1975): 1865–67. https://doi.org/10.1021/jo00900a052.Full Text
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Baldwin, S. W., and J. C. Tomesch. “Model Studies for the Synthesis of Tetracyclic Sesquiterpenes.” Synthetic Commun. 5, no. 6 (1975): 441.
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Baldwin, S. W., and J. C. Tomesch. “Stereospecific synthesis of d,l-cyclosativene. Alkyne capture of an homoallylic carbonium ion.” Tetrahedron Letters 16, no. 12 (January 1, 1975): 1055–58. https://doi.org/10.1016/S0040-4039(00)72643-8.Full Text
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Baldwin, S. W., and J. C. Tomesch. “Model Studies For The Synthesis Of Tetracyclic Sesquiterpenes.” Synthetic Communications 5, no. 6 (January 1, 1975): 445–50. https://doi.org/10.1080/00397917508065579.Full Text
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Baldwin, S. W., and R. E. Gawley. “Photoannelations with α-formyl ketones. A facile synthesis of the cis-9,10-dimethyldecalin ring system of the valerane sesquiterpenes.” Tetrahedron Letters 16, no. 46 (January 1, 1975): 3969–72. https://doi.org/10.1016/S0040-4039(00)91211-5.Full Text
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Baldwin, S. W., R. J. Doll, and S. A. Haut. “Selectivity in the Free-Radical Reduction of Lactones with Trichlorosilane.” Journal of Organic Chemistry 39, no. 16 (August 1, 1974): 2470–72. https://doi.org/10.1021/jo00930a053.Full Text
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Baldwin, S. W., and J. C. Tomesch. “Stereoselective Synthesis of 3-Exo-Substituted 2-endo-Acyl-5-norborene Derivatives.” Journal of Organic Chemistry 39, no. 16 (August 1, 1974): 2382–85. https://doi.org/10.1021/jo00930a011.Full Text
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Breslow, R., S. Baldwin, T. Flechtner, P. Kalicky, S. Liu, and W. Washburn. “Remote oxidation of steroids by photolysis of attached benzophenone groups.” Journal of the American Chemical Society 95, no. 10 (May 1973): 3251–62. https://doi.org/10.1021/ja00791a031.Full Text
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Baldwin, S. W., and E. H. Page. “Intramolecular keten cycloadditions in unconstrained systems.” Journal of the Chemical Society, Chemical Communications 0, no. 24 (December 1, 1972): 1337–38. https://doi.org/10.1039/C39720001337.Full Text
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Ireland, R. E., S. W. Baldwin, and S. C. Welch. “Experiments Directed toward the Total Synthesis of Terpenes. XVII. Development of Methods for the Synthesis of Pentacyclic Triterpenes Based on a Mechanistic Interpretation of the Stereochemical Outcome of the Friedel–Crafts Cyclialkylation Reaction.” Journal of the American Chemical Society 94, no. 6 (March 1, 1972): 2056–66. https://doi.org/10.1021/ja00761a044.Full Text
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Ireland, R. E., S. W. Baldwin, D. J. Dawson, M. I. Dawson, J. E. Dolfini, J. Newbould, W. S. Johnson, et al. “The Total Synthesis of an Unsymmetrical Pentacyclic Triterpene. DL-Germanicol.” Journal of the American Chemical Society 92, no. 19 (September 1, 1970): 5743–46. https://doi.org/10.1021/ja00722a041.Full Text
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Breslow, R., and S. W. Baldwin. “Conversion of Cholestanol to 12-Ketocholestanol and to Δ14- and Δ8(14)-Cholestenol by Remote Oxidation.” Journal of the American Chemical Society 92, no. 3 (February 1, 1970): 732–34. https://doi.org/10.1021/ja00706a068.Full Text
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Spencer, T. A., S. W. Baldwin, and K. K. Schmiegel. “Pyrolysis of 2-Acetoxy-2-(3-oxobutyl)cyclohexane-1,3-dione.” Journal of Organic Chemistry 30, no. 4 (April 1, 1965): 1294–96. https://doi.org/10.1021/jo01015a537.Full Text
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Spencer, T. A., M. D. Newton, and S. W. Baldwin. “Condensation of Diethyl Malonate with Methyl Vinyl Ketone.” Journal of Organic Chemistry 29, no. 4 (April 1, 1964): 787–89. https://doi.org/10.1021/jo01027a004.Full Text
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- Teaching & Mentoring
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Recent Courses
- CHEM 202D: Organic Chemistry II 2023
- CHEM 201DL: Organic Chemistry I 2022
- CHEM 202D: Organic Chemistry II 2022
- CHEM 201DL: Organic Chemistry I 2021
- CHEM 202D: Organic Chemistry II 2021
- CHEM 393: Research Independent Study 2021
- CHEM 394: Research Independent Study 2021
- CHEM 493: Research Independent Study 2021
- CHEM 494: Research Independent Study 2021
- CHEM 532: Organic Reactions 2021
- Scholarly, Clinical, & Service Activities
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Presentations & Appearances
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Service to the Profession
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