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Conformationally constrained dipeptides. Obtention of enantiomerically pure 6-acetamido-5-oxo-1,2,3,5,6,7-hexahydro-3-indolizine carboxylic acid

✍ Scribed by Régis Millet; Emmanuelle Meulon; Laurence Goossens; Raymond Houssin; Jean-Pierre Hénichart; Benoît Rigo

Publisher: Journal of Heterocyclic Chemistry
Year: 2000
Tongue: English
Weight: 276 KB
Volume: 37
Category: Article
ISSN: 0022-152X
DOI: 10.1002/jhet.5570370613

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✦ Synopsis

Abstract

The separation of a stereoisomeric mixture of esters 6, and the synthesis of the new enantiomerically pure unsaturated 6,5‐fused bicyclic lactam 2 are described. The key‐step involves trimethylsilyl iodide cleavage, without racemization, of a vinylogous carbamate. The cis N‐ acetylamino acid 2 is a new scaffold for the synthesis of rigid β‐turn mimetics.

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