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

来源：

TETRAHEDRON | 2000年 / 56卷 / 16期

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

页码：2437 / 2448

页数：12

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