Skip to main content
SpringerLink
Log in

New approach to the synthesis of 9-oxo-2E-decenoic acid, a multifunctional pheromone of queen honeybee, from the telomer of butadiene and water

  • Published:
Chemistry of Natural Compounds Aims and scope

A new approach was proposed for the synthesis of 9-oxo-2E-decenoic acid, a multifunctional pheromone of queen honeybee (Apis mellifera L.), starting from the available telomer of butadiene and water (2E,7-octadien-1-ol) using in the key steps partial ozonolysis of the corresponding carbonyl compound, selective oxidation of the conjugated aldehyde into a carboxylic acid, and alkylation of acetoacetic ester to introduce the oxo group.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Scheme 1

Similar content being viewed by others

References

  1. G. Yu. Ishmuratov, N. M. Ishmuratova, G. A. Tolstikov, A. F. Ismagilova, and A. A. Sharipov, Vestn. Ross. Akad. S-kh. Nauk, 81 (2003).

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

  3. U. M. Dzhemilev, V. V. Sidorova, and R. V. Kunakova, Izv. Akad. Nauk SSSR, Ser. Khim., 584 (1998).

  4. V. D. Komissarov, N. Ya. Shafikov, and Yu. S. Zimin, Kinet. Katal., 45, 514 (2004).

    Article  Google Scholar 

  5. J. F. W. McOmie, Protective Groups in Organic Chemistry, Plenum Press, New York, 1973.

    Google Scholar 

  6. D. Chakraborty, R. R. Gowda, and P. Malik, Tetrahedron Lett., 50, 6553 (2009).

    Article  CAS  Google Scholar 

  7. J. Kennedy, N. J. McCorkindale, and R. A. Raphael, J. Chem. Soc., 3813 (1961).

  8. K. Griesbaum, I. C. Jung, and H. Mertens, J. Org. Chem., 55, 6024 (1990).

    Article  CAS  Google Scholar 

  9. V. N. Odinokov, G. Yu. Ishmuratov, O. V. Sokol’skaya, R. I. Galeeva, R. R. Muslukhov, and G. A. Tolstikov, Zh. Org. Khim., 29, 24 (1993).

    CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Institute of Organic Chemistry, Ufa Scientific Center, Russian Academy of Sciences, 450054, Ufa, Russia

    G. Yu. Ishmuratov, V. A. Vydrina, G. V. Nasibullina, M. P. Yakovleva & R. R. Muslukhov

  2. N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch, Russian Academy of Sciences, Russia, 630090, Novosibirsk, Prosp. Akad. Lavrent’eva, 9

    G. A. Tolstikov

Authors
  1. G. Yu. Ishmuratov
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. V. A. Vydrina
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. G. V. Nasibullina
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. M. P. Yakovleva
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. R. R. Muslukhov
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. G. A. Tolstikov
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to G. Yu. Ishmuratov.

Additional information

Translated from Khimiya Prirodnykh Soedinenii, No. 5, September–October, 2011, pp. 693–695.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Ishmuratov, G.Y., Vydrina, V.A., Nasibullina, G.V. et al. New approach to the synthesis of 9-oxo-2E-decenoic acid, a multifunctional pheromone of queen honeybee, from the telomer of butadiene and water. Chem Nat Compd 47, 789–791 (2011). https://doi.org/10.1007/s10600-011-0060-9

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10600-011-0060-9

Keywords

Search

Navigation