New asymmetric syntheses of beta-hydroxy alpha-amino acids and analogues. Components of biologically active cyclopeptides

被引：22

作者：

Genet, JP

机构：

[1] Ecl. Natl. Sup. de Chimie de Paris, Lab. de Synthèse Organique, 75231 Paris Cedex 05

来源：

PURE AND APPLIED CHEMISTRY | 1996年 / 68卷 / 03期

关键词：

D O I：

10.1351/pac199668030593

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

MeBmt and analogues components of cyclosporine 2 were prepared by nucleophilic regioselective opening of chiral epoxyacids by methylamine. An efficient asymmetric hydrogenation-electrophilic amination sequence of beta-ketoesters allowed the production of and beta-hydroxy-alpha-amino acids present in cyclopeptides (luzopeptine, vancomycin). An ideal kinetic dynamic resolution of alpha-acylamido-beta-ketoester using ruthenium catalysts has been used for the production of L and D-threonine. This sequence war used for the preparation of (2S, 3R)-methyl-2-amino-3-(3'-chloro-4'-hydroxyphenyl) propionate precursor of a key component of vancomycin L.

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页码：593 / 596

页数：4

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