Shaanxi Key Laboratory of Natural Products and Chemical Biology, College of Chemistry and Pharmacy, North West Agriculture and Forestry University, Yangling 712100, China.
Shaanxi Key Laboratory for Catalysis, College of Chemical and Environment Science, Shaanxi University of Technology, Hanzhong 723001, China.
Molecules. 2018 Mar 15;23(3):667. doi: 10.3390/molecules23030667.
A convergent synthesis of four stereoisomers of the sex pheromone of the western corn rootworm (8-methyldecan-2-yl propionate, ) 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 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.
本文报道了从商业可得的手性起始原料出发，对西部玉米根萤叶甲性信息素（8-甲基十二烷-2-基丙酸酯，）的四个立体异构体进行收敛性合成。关键步骤是手性 BT-砜和手性醛之间的 Julia-Kocienski 烯烃化反应。该合成路线通过六步反应序列以 24-29%的总收率提供了四个立体异构体的。这种简单的放大策略为实现性信息素的不对称合成提供了新途径。
