Chemistry of Natural Compounds

, Volume 26, Issue 1, pp 78–82 | Cite as

Low-molecular-mass bioregulators. II. Synthesis of methyl (±)-tetradeca-2E,4,5-trienoate — The sex pheromone ofAcanthoscelides obtectus

  • G. G. Melikyan
  • V. M. Mkrtchyan
  • K. A. Atanesyan
  • G. Kh. Azaryan
  • Sh. O. Badanyan
Article

Abstract

A preparative method has been developed for obtaining methyl (±)-tetradeca-2E,4,5-trienoate — the racemate of the sex pheromone of the dried-bean beetle. Using methyl 4-chlorotetradec-5-ynoate as an example, a detailed study has been made of the dependence of the regiochemistry of reduction on the activity of a zinc-copper couple, the methods of its activation, and the acidity of the proton donor.

Keywords

Methyl Organic Chemistry Racemate Proton Donor Preparative Method 

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

Literature cited

  1. 1.
    G. G. Melikyan, D. A. Mkrtchyan, K. V. Lebedeva, U. Yu. Myaéorg, G. A. Panosyan, and Sh. O. Badanyan,Khim. Prir. Soedin., 98 (1984).Google Scholar
  2. 2.
    V. P. Valsil'ev,Pests of Agricultural Crops and Forest Plantations [in Russian], Vol. 2, Urozhai, Kiev (1974), p. 94.Google Scholar
  3. 3.
    D. F. Horler,J. Chem. Soc. (C), 859 (1970).Google Scholar
  4. 4.
    P. D. Landor, S. R. Landor, and S. Mukasa,J. Chem. Soc., Chem. Commun., 1638 (1971).Google Scholar
  5. 5.
    R. Bandouy and I. Gore,Synthesis, 573 (1974).Google Scholar
  6. 6.
    C. Descoins, C. A. Henrick, and B. Siddall,Tetrahedron Lett., 3773 (1972).Google Scholar
  7. 7.
    P. I. Kocienski, G. Cernigliaro, and G. Feldstein,J. Org. Chem. 42, 353 (1971).Google Scholar
  8. 8.
    A. P. Khrimyan and Sh. O. Badanyan,Arm. Khim. Zh. 32, 70 (1979).Google Scholar
  9. 9.
    B. Ledoussal, A. Gorgues, and A. Le Coo,Tetrahedron Lett., 51 (1981).Google Scholar
  10. 10.
    D. Michelot and G. Linstrummelle,Tetrahedron Lett., 275 (1976).Google Scholar
  11. 11.
    W. H. Pirkle and C. W. Boeder,J. Org. Chem. 43, 2091 (1978).Google Scholar
  12. 12.
    K. Mori, T. Nukada, and T. Ebata,Tetrahedron 27, 1343 (1981).Google Scholar
  13. 13.
    C. A. Henrick,Tetrahedron 33, 1877 (1977).Google Scholar
  14. 14.
    G. G. Melikyan, D. A. Mkrtchyan, and Sh. O. Badanyan,Arm. Khim. Zh. 35, 163 (1982).Google Scholar
  15. 15.
    Sh. O. Badanyan, G. G. Melikyan, and D. A. Mkrtchyan,Usp. Khim. 58, 475 (1989).Google Scholar
  16. 16.
    A. Takeda and T. Sakai,Bull. Chem. Soc. Jpn. 50, 1133 (1977).Google Scholar
  17. 17.
    Ya. I. Ginzberg,Zh. Obshch. Khim. 10, 513 (1940).Google Scholar
  18. 18.
    G. F. Hennion and J. J. Sheehan,J. Am. Chem. Soc. 71, 1964 (1949).Google Scholar
  19. 19.
    Ya. M. Slobodin,Zh. Obshch. Khim. 22, 1958 (1952).Google Scholar
  20. 20.
    T. H. Jacobs, E. G. Teach, and D. Weiss,J. Am. Chem. Soc. 77, 6254 (1955).Google Scholar
  21. 21.
    M. Bertrand,Bull. Soc. Chim. Fr., 461 (1956).Google Scholar
  22. 22.
    P. D. Landor, S. R. Landor, and E. S. Pepper,J. Chem. Soc. (C), 185 (1967).Google Scholar
  23. 23.
    A. T. Morse and L. S. Leitch,J. Org. Chem. 23, 990 (1958).Google Scholar
  24. 24.
    W. J. De Jarlais and E. A. Emken,Lipids 21, 662 (1986).Google Scholar
  25. 25.
    C. Verniere, B. Cazes, and J. Gore,Tetrahedron Lett., 103 (1981).Google Scholar
  26. 26.
    A. Mannschreck, W. Munninger, T. Burgemeister, J. Gore, and B. Cazes,Tetrahedron 42, 399 (1986).Google Scholar
  27. 27.
    R. A. Jacobson and W. H. Carothers,J. Am. Chem. Soc. 55, 1622 (1933).Google Scholar

Copyright information

© Plenum Publishing Corporation 1990

Authors and Affiliations

  • G. G. Melikyan
  • V. M. Mkrtchyan
  • K. A. Atanesyan
  • G. Kh. Azaryan
  • Sh. O. Badanyan

There are no affiliations available

Personalised recommendations