Chemistry of Natural Compounds

, Volume 18, Issue 2, pp 219–224 | Cite as

Pheromones of insects and their analogs. V. A new approach to the synthesis of the sex pheromones of insects of the orderLepidoptera which is based on the selective ozonolysis of 1-methylcycloocta-1Z,5Z-diene

  • G. A. Tolstikov
  • V. N. Odinokov
  • R. I. Galeeva
  • R. S. Bakeeva
  • V. R. Akhunova


A new synthesis of 1-acetoxyalk-Z-enes (sex pheromones of insects of the orderLepidoptera) has been developed which is based on the selective ozonolysis of 1-methylcycloocta-1Z-5Z-diene — a cooligomer of isoprene and butadiene.


Sulfolane Grignard Reagent Sodium Tetrahydroborate Hydroxy Ketone Ethyl Vinyl Ether 


Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

Literature cited

  1. 1.
    G. A. Tolstikov, B. N. Odinokov, R. J. Galeeva, R. S. Bakeeva, and V. R. Akhunova, Tetrahedron Lett., No. 50, 4851 (1979).Google Scholar
  2. 2.
    M. Jacobson, Insect Sex Pheromones, Academic Press, New York (1972).Google Scholar
  3. 3.
    Yu. A. Kondrat'ev, K. V. Lebedeva, and Yu. B. Tyatnova, Zh. Vses. Khim. Ova. in D. I. Mendeleeva,23, 179 (1978).Google Scholar
  4. 4.
    C. A. Henrick, Tetrahedron,33, 1845 (1977).CrossRefGoogle Scholar
  5. 5.
    V. N. Odinokov, R. S. Bakeeva, R. I. Galeeva, V. R. Akhunova, Ya. G. Mukhtatov, G. A. Tolstikov, L. M. Khalilov, and A. A. Panasenko, Zh. Org. Khim.,15, 2017 (1979).Google Scholar
  6. 6.
    R. O. Hutchins, C. A. Milewski, and B. E. Maryanoff, J. Am. Chem. Soc.,95, No. 11, 3662 (1973).CrossRefGoogle Scholar
  7. 7.
    L. Caglioti, Tetrahedron,22, 487 (1966).CrossRefGoogle Scholar
  8. 8.
    G. W. Gribble and D. C. Ferguson, J. Chem. Soc. Chem. Commun., No. 13, 535 (1975).Google Scholar
  9. 9.
    G. Budzikiewicz, C. Djerassi, and D. Williams, Interpretation of Mass Spectra of Organic Compounds, Holden-Day, San Francisco (1964).Google Scholar
  10. 10.
    D. Z. Struble and G. E. Swailes, Environ. Entomol.,4, 632 (1975).CrossRefGoogle Scholar
  11. 11.
    J. Borowitz, G. J. Williams, and L. Gross, J. Org. Chem.,33, 2016 (1968).Google Scholar
  12. 12.
    D. Goldsmith, E. Kennedy, and R. G. Campbell, J. Org. Chem.,40, 3571 (1975).CrossRefGoogle Scholar
  13. 13.
    S. W. Tinsley, E. A. Rick, and J. E. McKeon, US Patent No. 3,375,287 (1968).Google Scholar
  14. 14.
    C. F. Lane, Synthesis, 135 (1975).Google Scholar
  15. 15.
    J. Nokami, M, Kawada, and R. Okawara, Tetrahedron Lett., 1045 (1979).Google Scholar
  16. 16.
    G. Ohloff, C. Vial, F. Näf, and M. Pawlak, Helv. Chim. Acta,60, 1161 (1977).CrossRefGoogle Scholar
  17. 17.
    L. Fieser and M. Fieser, Reagents for Organic Synthesis, Wiley, New York (1967).Google Scholar
  18. 18.
    H. Matsuda, A. Jamamoto, N. Iwamoto, and S. Matsuda, J. Org. Chem.,43, 4567 (1978).CrossRefGoogle Scholar
  19. 19.
    A. Beckwith and P. Moad, J. Chem. Soc. Chem., Commun., 472 (1974).Google Scholar
  20. 20.
    O. Z. Chapman, K. C. Mattes, R. S. Sheridan, and J. A. Klun, J. Am. Chem. Soc.,100, 4878 (1978).CrossRefGoogle Scholar
  21. 21.
    J. Klein and J. Qarfinkee, J. Org. Chem.,34, 3952 (1969).CrossRefGoogle Scholar
  22. 22.
    M. Tamura and J. Kochi, Synthesis, 303 (1971).Google Scholar
  23. 23.
    H. J. Bestmann, K. H. Koschatzki, and O. Vostrowsky, Chem. Ber.,112, 1923 (1979).CrossRefGoogle Scholar
  24. 24.
    K. Kishino, K. Takahashi, S. Ando, and S. Tatsuki, Japanese Patent Application No. 54-49330 (1970).Google Scholar
  25. 25.
    E. W. Underhill, M. D. Chisholm, W. F. Steck, B. K. Bailey, P. M. Lamb, and D. L. Struble, US Patent No. 4,042,681 (1977).Google Scholar
  26. 26.
    L. Novak, M. Toth, J. Balla, and J. Szantay, Acta Chim. Acad. Sci. Hung.,102, 135 (1979).Google Scholar

Copyright information

© Plenum Publishing Corporation 1983

Authors and Affiliations

  • G. A. Tolstikov
  • V. N. Odinokov
  • R. I. Galeeva
  • R. S. Bakeeva
  • V. R. Akhunova

There are no affiliations available

Personalised recommendations