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

by 1,2,†, 1,†, 1, 1,3,* and 1,3,*
1
Shaanxi Key Laboratory of Natural Products and Chemical Biology, College of Chemistry and Pharmacy, North West Agriculture and Forestry University, Yangling 712100, China
2
Shaanxi Key Laboratory for Catalysis, College of Chemical and Environment Science, Shaanxi University of Technology, Hanzhong 723001, China
3
Key Laboratory of Botanical Pesticide R&D in Shaanxi Province, Yangling 712100, China
*
Authors to whom correspondence should be addressed.
These authors contributed equally to this work.
Molecules 2018, 23(3), 667; https://doi.org/10.3390/molecules23030667
Received: 11 February 2018 / Revised: 9 March 2018 / Accepted: 14 March 2018 / Published: 15 March 2018
(This article belongs to the Section Organic Chemistry)
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. View Full-Text
Keywords: pheromone; west corn rootworm; Evans methylation; Julia-Kocienski olefination; convergent synthesis pheromone; west corn rootworm; Evans methylation; Julia-Kocienski olefination; convergent synthesis
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MDPI and ACS Style

Sun, Z.-F.; Zhang, T.; Liu, J.; Du, Z.-T.; Zheng, H. Asymmetric Total Synthesis of Four Stereoisomers of the Sex Pheromone of the Western Corn Rootworm. Molecules 2018, 23, 667.

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