Synthesis of (1R,7Z)-1-methyl-7-hexadecenyl acetate, the female sex pheromone of the honey locust gall midge.
(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.
Photosensitive Materials Research Center, Toyo Gosei Co, Ltd, Inzai, Chiba, Japan.
Yasumasa
Y
Shikichi
Kenji
K
Mori
D000085:Acetates / Q000138:chemical synthesis*; D000818:Animals; D002683:Chironomidae / Q000737:chemistry* / Q000502:physiology; D005233:Fatty Alcohols / Q000737:chemistry*; D005260:Female; D008401:Gas Chromatography-Mass Spectrometry; D009682:Magnetic Resonance Spectroscopy; D012724:Sex Attractants / Q000138:chemical synthesis*; D013237:Stereoisomerism
C576385:1-methyl-7-hexadecenyl acetate; D000085:Acetates; D005233:Fatty Alcohols; D012724:Sex Attractants