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Highly stereoselective synthesis of a sex pheromone of the dry bean beetleCallosobruchus analis

  • Chemistry of Natural Compounds and Bioorganic Chemistry
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Russian Chemical Bulletin Aims and scope

Abstract

Total synthesis of 3-methylhept-2(Z)-enoic acid, a sex pheromone of the dry bean beetleCallosobruchus analis, has been performed using a previously developed highly stereoselective method of the construction of disubstituted (Z)-methylolefins based on the higher thermodynamic stability of (E)-isomers of α,β-disubstituted acroleins.

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References

  1. B. J. Southgate,Ann. Rev. Entomol., 1979,24, 449.

    Article  Google Scholar 

  2. A. Cork, D. R. Hall, W. M. Blanney, and M. S. Simmons,Tetrahedron Lett., 1991,32, 129.

    Article  CAS  Google Scholar 

  3. K. Ogura, T. Nishino, T. Koyama, and S. Seto,J. Am. Chem. Soc., 1970,92, 6036.

    Article  CAS  Google Scholar 

  4. N. Ya. Grigor'eva and O. A. Pinsker,Usp. Khim., 1994,63, 177 [Russ. Chem. Rev., 1994,63 (Engl. Transl.)].

    Google Scholar 

  5. N. Ya. Grigor'eva, I. M. Avrutov, O. A. Pinsker, O. N. Yudina, A. I. Lutsenko, and A. M. Moiseenkov,Izv. Akad. Nauk SSSR, Ser. Khim., 1985, 1824 [Bull. Acad. Sci. USSR, Div. Chem. Sci., 1985,34, 1673 (Engl. Transl.)].

  6. E. P. Prokof'ev, N. Ya. Grigor'eva, and A. V. Semenovskii,Izv. Akad. Nauk SSSR, Ser. Khim., 1980, 834 [Bull. Acad. Sci. USSR, Div. Chem. Sci., 1980,39, 586 (Engl. Transl.)].

  7. 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., 1979, 388 [Bull. Acad. Sci. USSR, Div. Chem. Sci., 1979,28 (Engl. Transl.)].

  8. E. J. Corey and K. Achiwa,J. Org. Chem., 1969,34, 3667.

    Article  CAS  Google Scholar 

  9. L. Palfray and S. Sabetay,Bull. Soc. Chim. Fr., 1937,4, 950.

    CAS  Google Scholar 

  10. J. Attenburrow, A. F. B. Cameron, J. H. Chapman, R. M. Evans, B. A. Hems, A. B. A. Jansen, and T. Walker,J. Chem. Soc., 1952, 1094.

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Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 7, pp. 1385–1388, July, 1999.

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Pinsker, O.A., Tsiklauri, P.G. & Grigor'eva, N.Y. Highly stereoselective synthesis of a sex pheromone of the dry bean beetleCallosobruchus analis . Russ Chem Bull 48, 1373–1375 (1999). https://doi.org/10.1007/BF02495308

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  • DOI: https://doi.org/10.1007/BF02495308

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