1. Asymmetric Total Synthesis of Four Stereoisomers of the Sex Pheromone of the Western Corn Rootworm
- Author
-
Tao Zhang, Zhen-Ting Du, Jinyang Liu, Zhi-Feng Sun, and Huaiji Zheng
- Subjects
Stereochemistry ,Convergent synthesis ,Pharmaceutical Science ,010402 general chemistry ,01 natural sciences ,Analytical Chemistry ,lcsh:QD241-441 ,pheromone ,lcsh:Organic chemistry ,convergent synthesis ,Drug Discovery ,Evans methylation ,Animals ,Physical and Theoretical Chemistry ,Sex Attractants ,chemistry.chemical_classification ,biology ,Molecular Structure ,010405 organic chemistry ,Communication ,Organic Chemistry ,Enantioselective synthesis ,Total synthesis ,Stereoisomerism ,biology.organism_classification ,Julia-Kocienski olefination ,0104 chemical sciences ,Coleoptera ,Western corn rootworm ,chemistry ,Chemistry (miscellaneous) ,Sex pheromone ,Propionate ,Molecular Medicine ,Pheromone ,west corn rootworm ,Propionates - Abstract
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.
- Published
- 2018