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

被引:28
作者
Langlois, N [1 ]
Rakotondradany, F [1 ]
机构
[1] CNRS, Inst Chim Subst Nat, F-91198 Gif Sur Yvette, France
关键词
3-hydroxy-4-methylproline; antifungals; (S)-pyroglutaminol; nitrone [3+2] cycloaddition; cope elimination; stereoselective hydrogenation;
D O I
10.1016/S0040-4020(00)00117-4
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
(2S,3S,4S)-3-Hydroxy-4-methylproline 2 was synthesized from unsaturated gamma-lactams 4 and 5 derived from (S)-pyroglutaminol. Starting from 5, haplophilic effect in the hydrogenation of a 4-exo-methylenic intermediate improved the diastereoselectivity of the synthesis, which was achieved in 19% yield. (C) 2000 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:2437 / 2448
页数:12
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