A chemo-enzymatic elaboration of a quarternary chiral center: an alternative approach to the side chain of furaquinocin D

被引：12

作者：

Akeboshi, T ^{[1
]}

Ohtsuka, Y ^{[1
]}

Sugai, T ^{[1
]}

Ohta, H ^{[1
]}

机构：

[1] Keio Univ, Dept Chem, Yokohama, Kanagawa 2238522, Japan

来源：

TETRAHEDRON | 1998年 / 54卷 / 26期

关键词：

D O I：

10.1016/S0040-4020(98)00400-1

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new approach to ethyl (2R, 3R)-2-t-butyldimethylsilyloxymethyl-3-hydroxy-2-methylbutanoate, a compound which is related to a synthetic intermediate of the side chain of furaquinocin D, is described. The characteristic feature of this compound is a quarternary chiral center and an adjacent secondary alcohol, both of which are in a stereochemically defined state, and the setup of these functionalities was achieved by a combination of stereoselective chemical and enzymatic reactions. The reduction of ethyl 2-hydroxymethyl-2-methyl-3-oxobutanoate with excess NaBH4 afforded (2R*,3R*)-(+/-)-hydroxy ester with a high diastereomeric excess. After protecting the primary hydroxy group as TBDMS ether, the optical resolution was achieved by lipase-catalyzed hydrolysis of the corresponding chloroacetate in a highly enantioselective manner. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：7387 / 7394

页数：8

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