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.

引用

页码：2164 / 2166

页数：3

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