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
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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- 4.B. G. Kovalev, R. I. Ishchenko, V. A. Marchenko, and M. P. Filippova, Zh. Org. Khim.,9, 6 (1973).Google Scholar
- 5.A. A. Shamshurin, M. A. Rekhter, and L. A. Vlad, Khim. Prir. Soedin., 545 (1973).Google Scholar
- 6.A. N. Kost, B. G. Kovalev, E. D. Matveeva, V. V. Stan, L. G. Yudin, Yu. A. Elizarov, and M. N. Barybkina, Bioorg. Khim.,3, 934 (1977).Google Scholar
- 7.G. A. Tolstikov, V. N. Odinokov, R. I. Galeeva, and R. S. Bakeeva, Tetrahedron, Lett., 1857 (1978).Google Scholar
- 9.V. N. Odinokov, R. I. Galeeva, R. S. Bakeeva, R. S. Grishova, and G. A. Tolsikov, Zh. Org. Khim.,15, 1403 (1979).Google Scholar
- 12.G. S. Bylina, G. A. Tolstikov, G. I. Rutman, P. N. Zernov, V. N. Odinokov, and U. M. Dzhemilev, USSR Inventor's Certificate No. 656,130, Byull. Izobret., No. 15, 21 (1979).Google Scholar