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Two approaches to the synthesis of 9-oxo-and 10-hydroxy-2E-decenoic acids, important components of queen substance and royal jelly of honeybees Apis mellifera

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Abstract

Two approaches to the synthesis of 9-oxo-and 10-hydroxy-2E-decenoic acids, biologically active components of queen substance and royal jelly of honeybees, respectively, were proposed starting with allyl bromide and 1,7-octadiene and using chemo-and regioselective transformations of the common intermediate building block 7-octen-1-ylacetate.

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References

  1. K. V. Lebedeva, V. A. Minyailo, and Yu. B. Pyatnova, Insect Pheromones [in Russian], Nauka, Moscow (1984).

    Google Scholar 

  2. G. Yu. Ishmuratov, A. F. Ismagilova, A. A. Sharipov, O. N. Gerasyuta, R. Ya. Kharisov, N. M. Ishmuratova, and G. A. Tolstikov, Khim.-farm. Zh., 37, 31 (2003).

    Google Scholar 

  3. N. M. Ishmuratova, G. Yu. Ishmuratov, G. A. Tolstikov, A. F. Ismagilova, and A. E. Belov, Vestn. Ross. Akad. Skh. Nauk, 84 (2007).

  4. Yu. B. Pyatnova, L. L. Ivanov, and A. S. Kyskina, Usp. Khim., 38, 248 (1969).

    CAS  Google Scholar 

  5. G. Yu. Ishmuratov, R. Ya. Kharisov, O. V. Botsman, N. M. Ishmuratova, and G. A. Tolstikov, Khim. Prir. Soedin., 3 (2002).

  6. G. Yu. Ishmuratov, M. P. Yakovleva, L. P. Botsman, N. M. Ishmuratova, R. R. Muslukhov, G. V. Khambalova, and G. A. Tolstikov, Khim. Prir. Soedin., 28 (2003).

  7. R. Chiron, J. Chem. Ecol., 8, 709 (1982).

    Article  CAS  Google Scholar 

  8. G. A. Tolstikov, V. N. Odinokov, R. I. Galeeva, R. S. Bakeeva, and V. R. Akhunova, Khim. Prir. Soedin., 239 (1982).

  9. V. N. Odinokov, G. Yu. Ishmuratov, L. P. Botsman, R. R. Vakhidov, I. M. Ladenkova, T. A. Kargapol’tseva, and G. A. Tolstikov, Khim. Prir. Soedin., 423 (1992).

  10. H. Matsuda, A. Yamamoto, N. Iwamoto, and S. Matsuda, J. Org. Chem., 43, 4567 (1978).

    Article  CAS  Google Scholar 

  11. G. Yu. Ishmuratov, M. P. Yakovleva, L. P. Botsman, N. M. Ishmuratova, R. R. Muslukhov, G. V. Khambalova, and G. A. Tolstikov, Khim. Prir. Soedin., 28 (2003).

  12. G. Yu. Ishmuratov, M. P. Yakovleva, G. V. Zaripova, A. V. Galyautdinova, L. P. Botsman, and N. M. Ishmuratova, Bashk. Khim. Zh., 36 (2004).

  13. Y. Katsumi, J. Chem. Soc. Jpn. Chem. Ind., 1415 (1978).

  14. V. N. Odinokov, G. Yu. Ishmuratov, and G. A. Tolstikov, Khim. Prir. Soedin., 695 (1983).

  15. Yu. K. Pyatraitis, Khemoretseptsiya Nasekomykh, 31 (1978).

  16. Yu. K. Pyatraitis, Khemoretseptsiya Nasekomykh, 213 (1975).

  17. Yu. K. Pyatraitis and V. K. Daukshas, Khemoretseptsiya Nasekomykh, 55 (1980).

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Correspondence to G. Yu. Ishmuratov.

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Translated from Khimiya Prirodnykh Soedinenii, No. 1, pp. 58–60, January–February, 2008.

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Ishmuratov, G.Y., Yakovleva, M.P., Tambovtsev, K.A. et al. Two approaches to the synthesis of 9-oxo-and 10-hydroxy-2E-decenoic acids, important components of queen substance and royal jelly of honeybees Apis mellifera . Chem Nat Compd 44, 74–76 (2008). https://doi.org/10.1007/s10600-008-0019-7

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  • DOI: https://doi.org/10.1007/s10600-008-0019-7

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