Insect pheromones and their analogs. VIII. Synthesis of the (Z) and (E) isomers of 2-methyloctadec-7-ene and of 2-methyl-7,8-epoxyoctadecane
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A highly stereospecific method for the synthesis of racemic (Z)-disparlure has been developed which is based on the reduction of 2-methyloctadec-7-yne with the aid of 9-borabicyclo[3.3.1]nonane and the epoxidation of the resulting (Z)-2-methyloctadec-7-ene with p-methoxycarbonylperbenzoic acid. The13C NMR spectra of the (Z) and (E) isomers of 2-methyloctadec-7-ene and 2-methyl-7,8-epoxyoctadecane, which unambiguously confirm the structures of these compounds, are given. It has been established that (E)-2-methyloctadec-7-ene exhibits a moderate attractant activity while the (Z) isomer does not attract the gypsy moth. The addition of 5–25% of (E)-disparlure increases the biological activity of (Z)-disparlure.
KeywordsEpoxide Gypsy Moth Epoxide Ring Ethylene Succinate Insect Pheromone
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