A TRANSKETOLASE-BASED SYNTHESIS OF (+)-EXO-BREVICOMIN

被引：58

作者：

MYLES, DC ^{[1
]}

ANDRULIS, PJ ^{[1
]}

WHITESIDES, GM ^{[1
]}

机构：

[1] HARVARD UNIV,DEPT CHEM,CAMBRIDGE,MA 02138

来源：

TETRAHEDRON LETTERS | 1991年 / 32卷 / 37期

基金：

美国国家卫生研究院;

关键词：

D O I：

10.1016/S0040-4039(00)93473-7

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The naturally occurring beetle pheromone (+)-exo-brevicomin was synthesized by a strategy combining chemical and enzymatic steps. The commercially available enzyme transketolase (EC 2.2.1.1) catalyzed the condensation of beta-hydroxypyruvic acid and 2-hydroxybutyraldehyde to furnish the central intermediate in the sequence, optically active hydroxyketone 5. A short sequence converted ketose 5 to protected aldose 8. Wittig extension of the aldehyde followed by hydrogenation and ketal hydrolysis generated the title compound.

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页码：4835 / 4838

页数：4

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