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Synthesis of 3S-methylundec-1-ylbromide, a key synthon in the synthesis of (S,S,S)-diprionylacetate, from L-(-)-menthol

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Abstract

Three new approaches to the synthesis of 1-bromo-3S-methylundecane, a key synthon in the synthesis of (S,S,S)-diprionylacetate, a sex pheromone of pine sawflies of the genera Diprion and Neodiprion, were proposed based on chemo-and stereoselective transformations of L-(-)-menthol derivatives.

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References

  1. K. Mori, Tetrahedron, 45, 3233 (1989).

    CAS  Google Scholar 

  2. G. Yu. Ishmuratov, M. P. Yakovleva, R. Ya. Kharisov, and G. A. Tolstikov, Usp. Khim., 1095 (1997).

  3. K. Mori, “Synthesis of insect pheromones,” in: J. ApSimon, ed., The Total Synthesis of Natural Products, Vol. 9, Wiley, New York (1992).

    Google Scholar 

  4. T. Kikukawa, M. Imaida, and A. Tai, Bull. Chem. Soc. Jpn., 57, No. 7, 1954 (1984).

    CAS  Google Scholar 

  5. R. L. Safiullin, A. N. Volgarev, G. Yu. Ishmuratov, M. P. Yakovleva, V. N. Odinokov, V. D. Komissarov, and G. A. Tolstikov, Dokl. Akad. Nauk SSSR, 316, 640 (1991).

    Google Scholar 

  6. W. Treibs and H. Albrecht, J. Prakt. Chem., 13, 291 (1961).

    CAS  Google Scholar 

  7. V. N. Odinokov, G. Yu. Ishmuratov, M. P. Yakovleva, R. L. Safiullin, A. N. Volgarev, V. D. Komissarov, and G. A. Tolstikov, Dokl. Akad. Nauk, 326, 842 (1992).

    CAS  Google Scholar 

  8. R. Ya. Kharisov, O. V. Botsman, R. R. Gazetdinov, G. Yu. Ishmuratov, and G. A. Tolstikov, Izv. Akad. Nauk, Ser. Khim., 1067 (2001).

  9. R. Ya. Kharisov, R. R. Gazetdinov, G. Yu. Ishmuratov, and G. A. Tolstikov, Khim. Prir. Soedin., 122 (2001).

  10. G. Yu. Ishmuratov, M. P. Yakovleva, V. A. Ganieva, R. R. Muslukhov, and G. A. Tolstikov, Khim. Prir. Soedin., 33 (2005).

  11. T. Kikukawa, M. Imaida, and A. Tai, Chem. Lett., 1799 (1982).

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Authors and Affiliations

  1. Institute of Organic Chemistry, Ufa Scientific Center, Russian Academy of Sciences, 450054, Ufa, pr. Oktyabrya, 71

    G. Yu. Ishmuratov, M. P. Yakovleva, R. Ya. Kharisov, A. M. Abulkaramova & G. A. Tolstikov

  2. Birsk State Social-Pedagogical Academy, 452320, RF, Birsk, ul. Internatsional’naya, 10

    V. A. Ganieva & R. R. Gazetdinov

Authors
  1. G. Yu. Ishmuratov
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  2. M. P. Yakovleva
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  3. V. A. Ganieva
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  4. R. Ya. Kharisov
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  5. R. R. Gazetdinov
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  6. A. M. Abulkaramova
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  7. G. A. Tolstikov
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Translated from Khimiya Prirodnykh Soedinenii, No. 1, pp. 73–76, January–February, 2006.

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Ishmuratov, G.Y., Yakovleva, M.P., Ganieva, V.A. et al. Synthesis of 3S-methylundec-1-ylbromide, a key synthon in the synthesis of (S,S,S)-diprionylacetate, from L-(-)-menthol. Chem Nat Compd 42, 92–95 (2006). https://doi.org/10.1007/s10600-006-0043-4

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  • DOI: https://doi.org/10.1007/s10600-006-0043-4

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