Russian Chemical Bulletin

, Volume 42, Issue 4, pp 760–763 | Cite as

Effective synthesis of femrrulactone II based on the use of 2-carhoxyethyltriphenylphosphonium bromide

  • B. A. Cheskis
  • N. A. Shpiro
  • A. M. Moiseenkov
Chemistry of Natural Compounds and Bioorganic Chemistry

Abstract

A simple synthesis ofS,3Z-dodecen-11-olide, a component of the aggregation pheromone of the rusty grain beetleCryptolestes ferrugineus (Stephen), was developed. The key stage was Wittig olefination of C9-aldehyde, prepared fromS-propylene oxide, with C3-phosphorane generated from the title phosphonium salt.

Key words

ferrulactone II 2-carboxyethyltriphenylphosphonium bromide S-propylene oxide S-8-(2-tetrahydropyranyloxy)nonanal Wittig reaction stereochemistry 

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. 1.
    J. W. Wong, V. G. Verigin, A. C. Oehlschlager, J. H. Borden, H. D. Pierce, Jr., A. M. Pierce, and L. Chong,J. Chem. Ecol., 1983,9, 451.Google Scholar
  2. 2.
    S. R. Loschiavo, J. W. Wong, N. D. G. White, H. D. Pierce, Jr., J. H. Borden, and A. C. Oehlschlager,Can. Entomol., 1986,118, 1.Google Scholar
  3. 3.
    A. C. Oehlschlager, J. W. Wong, V. G. Verigin, and H. D. Pierce, Jr.,J. Org. Chem., 1983,48, 5009.Google Scholar
  4. 4.
    T. Sakai and K. Mori,Agric. Biol. Chem., 1986,50, 177.Google Scholar
  5. 5.
    A. C. Oehlschlager, E. Czyzevska, R. Aksela. and H. D. Pierce, Jr.,Can. J. Chem., 1986,64, 1407.Google Scholar
  6. 6.
    G. A. Tolstikov, V. N. Odinokov, B. A. Cheskis, G. Yu. Ishmuratov, N. A. Shpiro, L. P. Botsman, M. V. Zlokazov, I. M. Ladenkova, and A. M. Moiseenkov,Dokl. Akad. Nauk SSSR, 1991,316, 642 [Dokl. Chem., 1991,316 (Engl. Transl.)].Google Scholar
  7. 7.
    E. Keinan, S. C. Sinha, and S. P. Singh,Tetrahedron, 1991,47, 4631.Google Scholar
  8. 8.
    T. Janecki and R. Bodalski,Tetrahedron Lett., 1991,32, 6231.Google Scholar
  9. 9.
    B. E. Maryanoff and A. B. Reitz,Chem. Rev., 1989,89, 863.Google Scholar
  10. 10.
    H. S. Corey, Jr., J. R. D. McCormick, and W. E. Swensen,J. Am. Chem. Soc., 1964,86, 1884.Google Scholar
  11. 11.
    M. M. Hann, P. G. Sammes, P. D. Kennewell, and J. B. Taylor,J. Chem. Soc., Perkin Trans, 1, 1982, 307.Google Scholar
  12. 12.
    B. E. Maryanoff, A. B. Reitz, and B. A. Duhl-Emswiller,J. Am. Chem. Soc., 1985,107, 217.Google Scholar
  13. 13.
    M. C. Stumpp and R. R. Schmidt,Tetrahedron, 1986,42, 5941.Google Scholar
  14. 14.
    S. R. Baker, D. W. Clissold, and A. M. McKillop,Tetrahedron Lett., 1988,29, 991.Google Scholar
  15. 15.
    V. S. Abdukakharov, M. M. Kasymzhanova, G. S. Shakirzanova, and A. A. Abduvakhabov,Khim. Prirod. Soed., 1990, 568 [Chem. Natur. Comp. (Engl. Transl.)].Google Scholar
  16. 16.
    N. Cohen, B. L. Banner, R. J. Lopresti, F. Wong, M. Rosenberg, Y.-Y. Liu, E. Thom, and A. A. Liebman,J. Am. Chem. Soc, 1983,105, 3661.Google Scholar
  17. 17.
    C. Prakash, S. Saleh, L. J. Roberts II, and I. A. Blair,J. Chem. Soc., Perkin Trans, 1, 1988, 2821.Google Scholar
  18. 18.
    C. Prakash, S. Saleh, and I. A. Blair,Synth. Commun., 1988,18, 2233.Google Scholar
  19. 19.
    H. Hoffmann,Chem. Ber., 1961,94, 1331.Google Scholar
  20. 20.
    S.-K. Kang, W.-S. Kim, and B.-H. Moon,Synthesis, 1985, 1161.Google Scholar

Copyright information

© Plenum Publishing Corporation 1994

Authors and Affiliations

  • B. A. Cheskis
    • 1
  • N. A. Shpiro
    • 1
  • A. M. Moiseenkov
    • 1
  1. 1.N. D. Zelinsky Institute of Organic ChemistryRussian Academy of SciencesMoscowRussian Federation

Personalised recommendations