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Synthesis from 10-undecenoic acid of octadeca-2E,13Z-dienylacetate, a component of the sex pheromones ofSynanthedon tipuliformis andZenzera pyrina

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Abstract

A new synthesis of octadeca-2E,13Z-dienylacetate from 10-undecenoic acid is developed by constructing the carbon framework of the pheromone in the key step and introducing the 2E double bond by Doebner condensation of hexadec-11-ynal and malonic acid.

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References

  1. S. Voerman, C. J. Persoons, and E. Priesner,J. Chem. Ecol.,10, 1371 (1984).

    Google Scholar 

  2. G. Szocs, M. Schwarz, G. Sziraki, M. Toth, J. A. Klun, and B. A. Leonhardt,Entomol. Exp. Appl.,39, 131 (1985).

    Google Scholar 

  3. C. Tonini, G. Cassani, P. Massardo, G. Guglielmetti, and P. L. Castellari,J. Chem. Ecol.,12, 1545 (1986).

    Google Scholar 

  4. A. M. Sorochinskaya and B. G. Kovalev,Khim. Prir. Soedin., 264 (1989).

  5. A. M. Sorochinskaya and B. G. Kovalev,Zh. Org. Khim:,27, 722 (1991).

    Google Scholar 

  6. M. Schwarz, J. A. Klun, B. A. Leonhardt, and D. T. Johnson,Tetrahedron Lett.,24, 1007 (1983).

    Google Scholar 

  7. F. Ramiandrasoa and C. Descoins,Synth. Commun.,19, 2703 (1989).

    Google Scholar 

  8. S. Narasimhan, H. Mohan, and S. Madhavan,Indian J. Chem., Sect. B,34, 531 (1995).

    Google Scholar 

  9. M. Hoskovec, D. Saman, and B. Koutek,Collect. Czech. Chem. Commun.,55, 2270 (1990).

    Google Scholar 

  10. G. Yu. Ishmuratov, M. P. Yakovleva, R. Ya. Kharisov, G. I. Kunafina, E. V. Gorobets, A. V. Kuchin, and G. A. Tolstikov,Izv. Akad. Nauk, Ser. Khim., 1529 (1977).

  11. K. Kh. Nguyen, M. V. Mavrov, and E. P. Serebryakov,Bioorg. Khim.,14, 250 (1988).

    Google Scholar 

  12. G. Yu. Ishmuratov, R. Ya. Kharisov, M. P, Yakovleva, O. V. Botsman, R. I. Galeeva, N. M. Ishmuratova, and G. A. Tolstikov,Izv. Akad. Nauk, Ser. Khim., 1637 (1998).

  13. V. N. Odinokov, G. Yu. Ishmuratov, R. R. Vakhidov, A. A. Berg, R. R. Muslukhov, and G.A. Tolstikov,Khim. Prir. Soedin., 272 (1992).

  14. V. N. Odinokov, G. Yu. Ishmuratov, I. M. Ladenkova, E. M. Vyrypaev, and G. A. Tolstikov,Khim. Prir. Soedin., 823 (1990).

  15. V. N. Odinokov, G. Yu. Ishmuratov, I. M. Ladenkova, and G. A. Tolstikov,Khim. Prir. Soedin., 440 (1987).

  16. V. N. Odinokov, G. Yu. Ishmuratov, I. M. Ladenkova, and G. A. Tolstikov,Khim. Prir. Soedin., 270 (1992).

  17. V. N. Odinokov, G. Yu. Ishmuratov, L. P. Botsman, I. M. Ladenkova, G. A. Tolstikov, U. M. Dzhemilev, A. G. Ibragimov, and D. L. Minsker, USSR Pat. No. 1566678, „Alkenynes as synthons for insect sex pheromones and their preparation.”

  18. G. Yu. Ishmuratov, Doctoral Dissertation in Chemical Sciences, IOC USC RAS, Ufa (1990).

  19. S. Gil, M. A. Lazaro, R. Mestres, and M. Parra,Synth. Commun.,26, 2329 (1996).

    Google Scholar 

  20. S. D. Razumovskii, S. K. Rakovski, D. M. Shopov, and G. E. Zaikov,Ozone and Its Reactions with Organic Compounds [in Russian], Izd. Bolgarskoi Akad. Nauk, Sofiya (1983).

    Google Scholar 

  21. U.S. Pat. No. 4571438 (1985);Ref. Zh. Khim., 22N28P (1986).

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Authors
  1. G. Yu. Ishmuratov
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  2. O. V. Botsman
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  3. L. P. Botsman
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  4. M. P. Yakovleva
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  5. R. Ya. Kharisov
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  6. G. A. Tolstikov
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Additional information

Institute of Organic Chemistry, Ufa Scientific Center, Russian Academy of Sciences, 450054, Ufa, prospekt Oktyabrya, 71, fax: (3472) 35 60 66. Translated from Khimiya Prirodnykh Soedinenii, No. 2, pp. 164–166, March–April, 2000.

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Ishmuratov, G.Y., Botsman, O.V., Botsman, L.P. et al. Synthesis from 10-undecenoic acid of octadeca-2E,13Z-dienylacetate, a component of the sex pheromones ofSynanthedon tipuliformis andZenzera pyrina . Chem Nat Compd 36, 207–209 (2000). https://doi.org/10.1007/BF02236432

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  • DOI: https://doi.org/10.1007/BF02236432

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