A synthetic approach to 3-hydroxy 4-substituted carboxylic acids based on the stereoselective reduction of 1-trimethyisilyl-1-alkyn-3-ones

被引：19

作者：

Alemany, C ^{[1
]}

Bach, J ^{[1
]}

Garcia, J ^{[1
]}

López, M ^{[1
]}

Rodríguez, AB ^{[1
]}

机构：

[1] Univ Barcelona, Div 3, Dept Quim Organ, E-08028 Barcelona, Catalonia, Spain

来源：

TETRAHEDRON | 2000年 / 56卷 / 47期

关键词：

oxazaborolidines; amino acids and derivatives; hydroxy acids and derivatives; reduction;

D O I：

10.1016/S0040-4020(00)00905-4

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The oxazaborolidine-mediated reduction of chiral, 4-substituted 1-trimethylsilyl-1-alkyn-3-ones followed by hydroboration affords syn or anti 3-hydroxy 4-substituted carboxylic acids, common substructures of a number of biologically active macrolides, peptides and depsipeptides, with high control on the new C(3) stereocenter. This strategy has been applied to the synthesis of (3S,4S)-3-hydroxy-4-methylheptanoic acid and of N-Boc-statine, constituents of permentin A and pepstatin, respectively. (C) 2000 Elsevier Science Ltd. All rights reserved.

引用

页码：9305 / 9312

页数：8

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