Abstract
A new synthesis of nonadeca-1,cis-3,cis-6,cis-9-tetraene, the sex pheromone of the winter mothOperophtera brumata, has been developed which involves the alkylation of bromomagnesium derivatives of tetrahydropyranyl ethers of mono- and diacetylenic alcohols by a monoacetylenic bromide, followed by hydrogenation of the resulting triynol to a trienol, oxidation of the latter to an aldehyde, and interaction of the latter with methylenetriphenylphosphorane.
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Literature cited
A. I. Vorontsov, Forest Entomology [in Russian], Vysshaya Shkola, Moscow (1967).
V. P. Vasil'ev and I. Z. Lifshits, Pests of Fruit Crops [in Russian], Kolos, Moscow (1984).
W. L. Roelofs, A. S. Hill, C. E. Linn, J. Meinwald, S. C. Jain, H. J. Herbert, and R. F. Swith, Science,217, 657–659 (1982).
H. J. Bestmann, T. Broche, K. H. Koschatzky, K. Michaelis, H. Platz, K. Roth, J. Sub, O. Vostrosky, and W. Knauf, Tetrahedron Lett.,23, No. 39, 4207 (1982).
S. C. Jain, W. L. Roelofs, and J. Meinwald, J. Org. Chem.,48, No. 13, 2274–2275 (1983).
W. Huang, S. P. Pulaski, and J. Meinwald, J. Org. Chem.,48, No. 13, 2270–2274 (1983).
R. Baker, M. J. O'Mahong, and C. Swain, J. Chem. Res. Syn.,6, 190–191 (1984).
E. W. Underhill, J. Chem. Ecol.,13, No. 6, 1319 (1987).
R. I. Ishchenko, B. G. Kovalev, and A. Kh. Khusid, Zh. Org. Khim,23, 1190–1193 (1987).
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All-Union Scientific-Research Institute for Biological Methods of Plant Protection, Moscow. Translated from Khimiya Prirodnykh Soedinenii, No. 1, pp. 122–125, January–February, 1992.
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Nikolaeva, L.A., Kovalev, B.G. & Ishchenko, R.I. Synthetic studies in the field of attractive substances (sex attractants) of insects. Chem Nat Compd 28, 103–105 (1992). https://doi.org/10.1007/BF00629805
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DOI: https://doi.org/10.1007/BF00629805