Synthesis of (1R,7Z)-1-Methyl-7-hexadecenyl Acetate, the Female Sex Pheromone of the Honey Locust Gall Midge

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(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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