Chemistry Letters
Online ISSN : 1348-0715
Print ISSN : 0366-7022
ISSN-L : 0366-7022
A Synthesis of (3S,4R)-3-[(R)-1-(t-Butyldimethylsilyloxy)ethyl]-4-carboxymethyl-2-azetidinone, the Thienamycin Intermediate, from (S)-Ethyl Lactate
Yoshio ItoShiro Terashima
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1987 Volume 16 Issue 3 Pages 445-448

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Abstract

The title thienamycin intermediate was efficiently synthesized from (S)-ethyl lactate (3) by subjecting (3S,4S)-3-acetyl-4-[(S)-1-benzyloxyethyl]-2-azet idi none readily obtainable from 3, to sequential reactions in which base catalyzed elimination and regioselective hydroboration were employed as the key processes.

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