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Rigid Dipeptide Mimetics: Efficient Synthesis of Enantiopure Indolizidinone Amino Acids

✍ Scribed by Lombart, Henry-Georges; Lubell, William D.

Book ID: 115315502
Publisher: American Chemical Society
Year: 1996
Tongue: English
Weight: 557 KB
Volume: 61
Category: Article
ISSN: 0022-3263
DOI: 10.1021/jo961872f

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Short syntheses are presented of the pseudo-dipeptide (3S,6S)-6-[(benzyloxy)carbonyl]amino-5-oxo-1,2,3,5,6,7-hexahydro-3-indolizinecarboxylic acid (1a) and of its (3S,6R) diastereoisomer (1b). The key step involves adding vinylogous b-enaminoester derived from pyroglutamic acid on an acrylate deriva