一种简洁、无保护基、发散的方法，用于合成秋野蛾和其他物种的两种信息素环氧化物成分的对映选择性合成。

A concise, protection-free and divergent approach for the enantioselective syntheses of two pheromonal epoxide components of the fall webworm moth and other species.

机构信息

Department of Chemistry and Key Laboratory for Chemical Biology of Fujian Province, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, Fujian 361005, People's Republic of China.

出版信息

J Org Chem. 2010 Jul 2;75(13):4619-22. doi: 10.1021/jo1007042.

DOI:10.1021/jo1007042

PMID:20507127

Abstract

On the basis of Zhou's modified Sharpless asymmetric epoxidation, sequential coupling reactions, and a divergent strategy, the protection-free syntheses of two main pheromonal components 1 and 5, found in the fall webworm moth, Hyphantria cunea, and other species have been accomplished in 10 steps (for two compounds). The overall yields are 31% for 1, 28% for 5, and 25% for both 1 and 5, respectively. The ee values of the final products 1 and 5 are at least 99%.

摘要

基于周环反应的Sharpless 不对称环氧化反应、连续偶联反应和发散策略，以保护基自由的方式完成了秋粘虫（Hyphantria cunea）及其它种属的两种主要信息素成分 1 和 5 的合成，共 10 步（针对两种化合物）。总收率分别为 1 的 31%、5 的 28%以及 1 和 5 的 25%。最终产物 1 和 5 的对映体过量值至少为 99%。