Diastereoselective synthesis of (2S,3S,4S)-3-hydroxy-4-methylproline, a common constituent of several antifungal cyclopeptides

Authors
Langlois, N Rakotondradany, F
Citation
N. Langlois et F. Rakotondradany, Diastereoselective synthesis of (2S,3S,4S)-3-hydroxy-4-methylproline, a common constituent of several antifungal cyclopeptides, TETRAHEDRON, 56(16), 2000, pp. 2437-2448
Citations number
54
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON
ISSN journal
00404020 → ACNP
Volume
56
Issue
16
Year of publication
2000
Pages
2437 - 2448
Database
ISI
SICI code
0040-4020(20000414)56:16<2437:DSO(AC>2.0.ZU;2-6
Abstract
(2S,3S,4S)-3-Hydroxy-4-methylproline 2 was synthesized from unsaturated gam ma-lactams 4 and 5 derived from (S)-pyroglutaminol. Starting from 5, haplop hilic effect in the hydrogenation of a 4-exo-methylenic intermediate improv ed the diastereoselectivity of the synthesis, which was achieved in 19% yie ld. (C) 2000 Elsevier Science Ltd. All rights reserved.