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Thienamycin. A solution of the Stereochemical Problem

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Tue, 2014-04-01 10:50 — Mohammed Abdullah Al-Nuri
Journal Title, Volume, Page: 
Tetrahedron Letters Volume 20, Issue 45, Pages 4359–4362
Year of Publication: 
1979
Link: 
http://www.sciencedirect.com/science/article/pii/S0040403901865886
Authors: 
Mohammed Al-Nuri
Department of Chemistry State University of New York at Buffalo Bufflo, NY 14214 U.S.A
Current Affiliation: 
Department of Chemistry, Faculty of Science, An-Najah National University, Nablus, Palestine
[email protected]
Joseph J. Tufariello
Department of Chemistry State University of New York at Buffalo Bufflo, NY 14214 U.S.A
George E. Lee
Department of Chemistry State University of New York at Buffalo Bufflo, NY 14214 U.S.A
Pushpananda A. Senaratne
Department of Chemistry State University of New York at Buffalo Bufflo, NY 14214 U.S.A
Preferred Abstract (Original): 

A new nitrone-based synthesis of β-lactams is described which makes provision for the 1-hydroxyethyl moiety in the potent antibiotic thienamycin. Moreover, the relative stereochemical features of the natural product are defined in a step involving the cycloaddition of a nitrone with methyl crotonate.