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Stereoselective Syntheses of Tetrahydroesterastin-β -Lactam Analogues

✍ Scribed by Isabelle Huber; Fernand Schneider

Publisher
John Wiley and Sons
Year
1994
Tongue
German
Weight
773 KB
Volume
77
Category
Article
ISSN
0018-019X

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✦ Synopsis

A total synthesis of the optically active tetrahydroesterastinB -1actam analogue 2 using MilZer's hydroxamate approach is described (Scheme 2). Significant modification of published procedures has resulted in a short and facile stereospecific preparation of the N-[(benzyloxycarbonyl)methyl]$ -1actam 17 starting from the readily available o-serine. This material served as intermediate for the preparation of a variety of N-[(benzyloxycarbonyl)methyl]tetrahydroesterastinP -1actam analogues (Scheme 5 ) .

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✍ Alan D. Brown; Ernest W. Colvin 📂 Article 📅 1991 🏛 Elsevier Science 🌐 French ⚖ 127 KB

An efficient method for the preparation of chiral cis-3,4-disubstituted 8-1actams, based on reaction between imines from homochiral protected lactaldehydes and furfurylamine and phenyl dichlorophosphate activated carboxylic acid derivatives, is reported.