Asymmetric synthesis of (2R,5S)-2-methyl-5-hexanolide, the sex pheromone of carpenter bee Xylocopa hirutissima

被引：10
作者：
Yang, Jian-Hong
Yang, Gui-Chun [1 ]
Lu, Cui-Fen
Chen, Zu-Xing
机构：
[1] Hubei Univ, Minist Educ, Key Lab Synth & Applicat Organ Funct Mol, Wuhan 430062, Peoples R China
来源：
TETRAHEDRON-ASYMMETRY | 2008年 / 19卷 / 18期
关键词：
D O I：
10.1016/j.tetasy.2008.08.026
中图分类号：
O61 [无机化学];
学科分类号：
070301 ; 081704 ;
摘要：
The stereoselective synthesis of the (2R,5S)-2-methyl-5-hexanolide, a sex pheromone of Xylocopa hirutissima, has been achieved in 6 steps and 33% overall yield. The synthesis relies on an asymmetric N-acetyl thiazolidinethione aldol reaction to establish the C5 stereogenic centers. The remaining stereogenic center at C2 was set through a N-propionylprolinol-mediated asymmetric alkylation reaction. (C) 2008 Elsevier Ltd. All rights reserved.
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页码：2164 / 2166
页数：3
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