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Insect pheromones and their analogues

XXXIV. Chiral pheromones from (S)-(+)-3,7-dimethylocta-1,6-diene. 2. Synthesis of optically active (S)-(−)-diprionyl acetate configurationally homogeneous with respect to the C3 atom

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Abstract

A four-stage synthesis has been performed of the optically active (S)-(−)-diprionyl acetate in the form of an equimolar mixture of erythro-(2S,3S,7SR)- and threo-(2R,3S,7SR)-2-acetoxy-3,7-dimethylpentadecanes from a readily available chiral compound — (S)-(+)-3,7-dimethylocta-1,6-diene — with an overall yield of 13%.

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Literature cited

  1. F. Matsumura, A. Tai, H. C. Coppel, and M. Imaida, J. Chem. Ecol.,5, No. 2, 237 (1979).

    Google Scholar 

  2. M. Kraemer, H. C. Coppel, F. Matsumura, T. Kikukawa, and K. Mori, Environ. Entomol.,8, No. 3, 519 (1979).

    Google Scholar 

  3. T. Kikukawa, F. Matsumura, J. Olaifa, M. Kraemer, H. C. Coppel, and A. Tai, J. Chem. Ecol.,9, No. 6, 673 (1983).

    Google Scholar 

  4. V. N. Odinokov, G. Yu. Ishnuratov, R. Ya. Kharisov, and G. A. Tolstikov, Khim. Prir. Soedin., No. 4, 573 (1989).

  5. Nguen Kong Khao, M. V. Mavrov, and É. P. Serebryakov, Izv. Akad. Nauk SSSR, Ser. Khim., No. 5, 1142 (1989).

  6. K. Mori, S. Tamada, and M. Matsui, Tetrahedron Lett.,39, No. 10, 901 (1978).

    Google Scholar 

  7. K. Mori and S. Tamada, Tetrahedron,35, No. 10, 1279 (1979).

    Google Scholar 

  8. S. Byström, H. E. Hogberg, and T. Morin, Tetrahedron,37, No. 12, 2249 (1981).

    Google Scholar 

  9. T. Kikukawa, M. Imaida, and A. Tai, Bull. Chem. Soc. Jpn.,57, No. 7, 1954 (1984).

    Google Scholar 

  10. S. S. Poddubnaya, V. G. Cherkaev, and S. A. Voitkevich, Khim. Drev., No. 4, 93 (1983).

  11. J. Tsuji, Synthesis, No. 5, 369 (1984).

  12. D. M. Jewett, F. Matsumura, and H. C. Coppel, Science,192, No. 4234, 47 (1976).

    Google Scholar 

  13. G. Magnusson, Tetrahedron,34, No. 9, 1385 (1978).

    Google Scholar 

  14. K. Sato, S. Inoue, A. Onishi, N. Uchida, and N. Minowa, J. Chem. Soc., Perkin Trans. I, No. 3, 761 (1981).

    Google Scholar 

  15. A. S. Shashkov, N. Ya. Grigor'eva, I. M. Avrutov, A. V. Semenovskii, V. N. Odinokov, V. K. Ignatyuk, and G. A. Tolstikov, Izv. Akad. Nauk SSSR, Ser. Khim., No. 2, 388 (1979).

  16. Nguen Kong Khao, M. V. Mavrov, and É. P. Serebryakov, Zh. Org. Khim.,23, No. 8, 1649 (1987).

    Google Scholar 

  17. F. J. McQuillin and D. G. Parker, J. Chem. Soc., Perkin Trans. I, No. 7, 809 (1974).

    Google Scholar 

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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. 117–122, January–February, 1992.

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Odinokov, V.N., Ishmuratov, G.Y., Ladenkova, I.M. et al. Insect pheromones and their analogues. Chem Nat Compd 28, 98–102 (1992). https://doi.org/10.1007/BF00629804

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  • DOI: https://doi.org/10.1007/BF00629804

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