Stereoselective chemoenzymatic synthesis of sitophilate: a natural pheromone

被引：20
|
作者：
Kalaitzakis, Dimitris [1 ]
Kambourakis, Spiros [2 ]
Rozzell, David J. [2 ]
Smonou, Ioulia [1 ]
机构：
[1] Univ Crete, Dept Chem, Iraklion, Greece
[2] Codexis Inc, Pasadena, CA 91106 USA
来源：
TETRAHEDRON-ASYMMETRY | 2007年 / 18卷 / 20期
关键词：
D O I：
10.1016/j.tetasy.2007.10.008
中图分类号：
O61 [无机化学];
学科分类号：
070301 ; 081704 ;
摘要：
The aggregation pheromone of the granary weevil Sitophilus granarius, (2S,3R)-1-ethylpropyl 3-hydroxy-2-methylpentanoate, has been synthesized in 63% total isolated yield and high chemical and enantiomeric purity (98% de, > 99% ee) from readily available methyl 3-oxopentanoate. A stereoselective ketone reduction followed by an ester hydrolysis, were the two key steps of the synthesis and were both performed by commercially available enzymes. (c) 2007 Elsevier Ltd. All rights reserved.
引用
收藏
页码：2418 / 2426
页数：9
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