Abstract
A scheme has been developed for the synthesis of (R)-(−)-10-methyltridecan-2-one, the sex pheromone of the southern corn rootworm (Diabrotica undecimpunctata) using as the chiral synthon (R)-(+)-methylheptenal obtained by the hydroperoxide oxidation of the readily available (S)-(+)-dihydromyrcene.
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Literature cited
P. L. Guss, J. H. Tumlinson, I. R. McLaughlin, and P. E. Sonnet, J. Chem. Ecol.,9, No. 9, 1363 (1983).
P. E. Sonnet, J. Chem. Chem.,47, No. 19, 3793 (1982).
S. Senda and K. Mori, Agr. Biol. Chem.,47, No. 4, 795 (1983).
R. Rossi, A. Carpita, and H. Chini, Tetrahedron,41, No. 3, 627 (1985).
Nguen Kong Khao and N. V. Mavrov, Izv. Akad. Nauk SSSR, Ser. Khim., No. 9, 2083 (1987).
Nguen Kong Khao, M. V. Mavrov, É. P. Serebryakov, and S. V. Shavyrin, USSR Inventors' Certificate No. 1,284,979 (1987); Byull. Izobret., No. 3, 108 (1987).
T. L. Cairns and B. E. Englund, J. Org. Chem.,21, No. 1, 140 (1956).
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Institute of Chemistry, Bashkir Scientific Center, Urals Branch, Russian Academy of Sciences, Ufa. Translated from Khimiya Prirodnykh Soedinenii, No. 1, pp. 125–129, January–February, 1992.
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Odinokov, V.N., Kukovinets, O.S., Kasradze, V.G. et al. Insect pheromones and their analogues. Chem Nat Compd 28, 106–109 (1992). https://doi.org/10.1007/BF00629806
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DOI: https://doi.org/10.1007/BF00629806