Asymmetric Total Synthesis of Four Stereoisomers of the Sex Pheromone of the Western Corn Rootworm

Molecules

Zhen-Ting Du¹  Tao Zhang¹  Jinyang Liu¹  Zhi-Feng Sun¹  Huaiji Zheng¹ 

[1] Shaanxi Key Laboratory of Natural Products and Chemical Biology, College of Chemistry and Pharmacy, North West Agriculture and Forestry University, Yangling 712100, China;

关键词: pheromone;    west corn rootworm;    Evans methylation;    Julia-Kocienski olefination;    convergent synthesis;   

DOI  :  10.3390/molecules23030667

来源: DOAJ

【 摘 要 】

A convergent synthesis of four stereoisomers of the sex pheromone of the western corn rootworm (8-methyldecan-2-yl propionate, 1) from commercially available chiral starting materials is reported. The key step was Julia–Kocienski olefination between chiral BT-sulfone and chiral aldehyde. This synthetic route provided the four stereoisomers of 1 in 24–29% total yield via a six-step sequence. The simple scale-up strategy provides a new way to achieve the asymmetric synthesis of the sex pheromone.

【 授权许可】

Unknown