Stereoselective reduction of α′-branched α,β-ynones.: Application to the synthesis of the Octalactin A ring

被引：25

作者：

Bach, J ^{[1
]}

Garcia, J ^{[1
]}

机构：

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

来源：

TETRAHEDRON LETTERS | 1998年 / 39卷 / 37期

关键词：

diastereoselection; marine metabolites; oxazaborolidines; reduction;

D O I：

10.1016/S0040-4039(98)01420-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A flexible, efficient route to chiral 3-hydroxy-4-methyl- and 3-hydroxy-4-methoxyalkanoic acids, with high control of the C(3) configuration, has been disclosed, which is based on the borane-mediated reduction of 1-trimethylsilyl-1-alkyn-3-ones (6) in the presence of oxazaborolidine 7 followed by hydroboration of the resulting propargylic alcohols 4 and 5. This strategy has been applied to the synthesis of the Octalactin A ring. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：6761 / 6764

页数：4

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