Novel, stereoselective syntheses of penem antibiotics: efficient, formal syntheses of SCH 34343
Publication
, Journal Article
Hou, D; Mas, JL; Chan, TM; Wong, YS; Steinman, M; McPhail, AT
Published in: 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-azetidinone (22), key intermediates in the synthesis of the penem antibiotic Sch 34343, were developed starting from readily available 6-aminopenicillanic acid. Advantages of these routes include 1) the highly stereospecific introduction of the hydroxyethyl sidechain with the desired (R)-configuration and 2) the retention of the sulfur of the starting material. © 1993.
Duke Scholars
Published In
Bioorganic and Medicinal Chemistry Letters
DOI
ISSN
0960-894X
Publication Date
January 1, 1993
Volume
3
Issue
11
Start / End Page
2171 / 2176
Related Subject Headings
- Medicinal & Biomolecular Chemistry
- 3405 Organic chemistry
- 3404 Medicinal and biomolecular chemistry
- 1115 Pharmacology and Pharmaceutical Sciences
- 0305 Organic Chemistry
- 0304 Medicinal and Biomolecular Chemistry
Citation
APA
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ICMJE
MLA
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Hou, D., Mas, J. L., Chan, T. M., Wong, Y. S., Steinman, M., & McPhail, A. T. (1993). Novel, stereoselective syntheses of penem antibiotics: efficient, formal syntheses of SCH 34343. Bioorganic and Medicinal Chemistry Letters, 3(11), 2171–2176. https://doi.org/10.1016/S0960-894X(01)80920-3
Hou, D., J. L. Mas, T. M. Chan, Y. S. Wong, M. Steinman, and A. T. McPhail. “Novel, stereoselective syntheses of penem antibiotics: efficient, formal syntheses of SCH 34343.” Bioorganic and Medicinal Chemistry Letters 3, no. 11 (January 1, 1993): 2171–76. https://doi.org/10.1016/S0960-894X(01)80920-3.
Hou D, Mas JL, Chan TM, Wong YS, Steinman M, McPhail AT. Novel, stereoselective syntheses of penem antibiotics: efficient, formal syntheses of SCH 34343. Bioorganic and Medicinal Chemistry Letters. 1993 Jan 1;3(11):2171–6.
Hou, D., et al. “Novel, stereoselective syntheses of penem antibiotics: efficient, formal syntheses of SCH 34343.” Bioorganic and Medicinal Chemistry Letters, vol. 3, no. 11, Jan. 1993, pp. 2171–76. Scopus, doi:10.1016/S0960-894X(01)80920-3.
Hou D, Mas JL, Chan TM, Wong YS, Steinman M, McPhail AT. Novel, stereoselective syntheses of penem antibiotics: efficient, formal syntheses of SCH 34343. Bioorganic and Medicinal Chemistry Letters. 1993 Jan 1;3(11):2171–2176.
Published In
Bioorganic and Medicinal Chemistry Letters
DOI
ISSN
0960-894X
Publication Date
January 1, 1993
Volume
3
Issue
11
Start / End Page
2171 / 2176
Related Subject Headings
- Medicinal & Biomolecular Chemistry
- 3405 Organic chemistry
- 3404 Medicinal and biomolecular chemistry
- 1115 Pharmacology and Pharmaceutical Sciences
- 0305 Organic Chemistry
- 0304 Medicinal and Biomolecular Chemistry