Synthesis of (1R,7Z)-1-methyl-7-hexadecenyl acetate, the female sex pheromone of the honey locust gall midge

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Abstract

(1R,7Z)-1-Methyl-7-hexadecenyl acetate (1), the female sex pheromone of the honey locust gall midge (Dasineura gleditchiae), was synthesized from 6-hepten-1-ol in an 8.9% overall yield (eight steps). Hydrolytic kinetic resolution of (±)-1,2-epoxy-8-heptadecyne was the key step in the synthesis.

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Shikichi, Y., & Mori, K. (2012). Synthesis of (1R,7Z)-1-methyl-7-hexadecenyl acetate, the female sex pheromone of the honey locust gall midge. Bioscience, Biotechnology and Biochemistry, 76(7), 1419–1421. https://doi.org/10.1271/bbb.120265

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