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β-lactams from azetidine carboxylates. A synthesis of (1-3-ana, the nucleus of the nocardicins

✍ Scribed by Harry H. Wasserman; Alan W. Tremper; James S. Wu

Publisher
Elsevier Science
Year
1979
Tongue
French
Weight
202 KB
Volume
20
Category
Article
ISSN
0040-4039

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✦ Synopsis

Sunmary:

A synthesis of (+)-3-ANA is described involving oxidative decarbonylation of an azetidine carboxylic ester.

We have recently described new methods for the formation of B-lactams by the oxidative decarboxylation 133 or decarbonylation2 of azetidine-2-carboxylic acids. We now report the application of one of these procedures2 to the synthesis of (t)-3-aminonocardicinic acid (S-ANA) (XII), the nucleus of the nocardicins, 8-lactam antibiotics recently isolated from a strain of Nocardia.4y5

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## Abstract Chlorozinc enolates of (hetero)aryl‐, alkyl‐ and silyl‐substituted acetates were reacted with imines and α‐diimines. The zinc‐mediated reaction of (hetero)aryl‐substituted acetates with imines afforded __trans__‐β‐lactams in good yields and with excellent selectivity. Zinc enolates of n