Skip to main content
SpringerLink
Log in

Synthesis and transformations of 20-oxo-30-nortaraxasteryl acetate derivatives

  • Published:
Russian Journal of Organic Chemistry Aims and scope Submit manuscript

Abstract

20,20-Dimethoxy-, Δ21-20-oxo-, and 20-oxo-30-nortaraxasteryl acetates were synthesized by selective ozonolysis of taraxasteryl acetate. Baeyer-Villiger oxidation of 20-oxo-30-nortaraxasteryl acetate with SeO2-H2O2 gave 3β-acetoxytaraxa-(19,20)-ɛ-lactone. Mechanism of the ozonolysis of taraxasteryl acetate is discussed. The enthalpies of formation of possible intermediates were calculated by quantum-chemical methods, and most favorable paths of the ozonolysis and dehydrogenation were determined.

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

Similar content being viewed by others

References

  1. Khalilov, L.M., Khalilova, A.Z., Shakurova, E.R., Nuriev, I.F., Kachala, V.V., Shashkov, A.S., and Dzhemilev, U.M., Khim. Prirodn. Soedin., 2003, p. 223.

  2. Mahato, S.B. and Sen, S., Phytochemistry, 1997, vol. 44, p. 1185.

    Article  CAS  Google Scholar 

  3. Dai, J., Zhao, Ch., Zhang, Q., Liu, Z., Zheng, R., and Yang, L., Phytochemistry, 2001, vol. 58, p. 1107.

    Article  CAS  Google Scholar 

  4. Zitteri-Eglseer, K., Sosa, S., Jurenitsch, J., Schubert-Zsilavecz, M., Della, L.R., Tubaro, A., Bertoldi, M., and Franz, C., J. Ethnopharm., 1997, vol. 57, p. 139.

    Article  Google Scholar 

  5. Yasukawa, K., Akihisa, T., Oinuma, H., Kaminaga, T., Kanno, H., Kasahara, Y., Tamura, T., Kumaki, K., Yamanouchi, S., and Takiao, M., Oncology, 1996, vol. 53, p. 341.

    Article  CAS  Google Scholar 

  6. Boguslaw, J., US Patent Appl. no. 10 353 483, 2003.

  7. Chiang, Y.M. and Kuo, Y.H., J. Nat. Prod., 2000, vol. 63, p. 898.

    Article  CAS  Google Scholar 

  8. Pai, P.P. and Kulkarni, G.H., Indian J. Chem., Sect. B, 1977, vol. 15, p. 959.

    Google Scholar 

  9. Odinokov, V.N., Akhunova, V.R., Bakeeva, R.S., Galeeva, R.I., Semenovskii, A.V., Moiseenkov, A.M., and Tolstikov, G.A., Zh. Org. Khim., 1977, vol. 13, p. 532.

    CAS  Google Scholar 

  10. Rao, C.N.R. Ultra-violet and Visible Spectroscopy: Chemical Applications, London: Butterworths, 1961. Translated under the title Elektronnye spektry v khimii, Moscow: Mir, 1964, p. 57.

    Google Scholar 

  11. Peng, H., Otterness, D.M., Abraham, R.T., and Zalkow, L.H., Tetrahedron, 2001, vol. 57, p. 1891.

    Article  CAS  Google Scholar 

  12. Paryzek, Z., Koenig, H., Skiera, I., and Rychlewska, U., Polish J. Chem., 2002, vol. 76, p. 921.

    CAS  Google Scholar 

  13. Odinokov, V.N. and Tolstikov, G.A., Usp. Khim., 1981, vol. 50, p. 1207.

    CAS  Google Scholar 

  14. Razumovskii, S.D. and Zaikov, G.E., Ozon i ego reaktsii s organicheskimi soedineniyami (Ozone and Its Reactions with Organic Compounds), Moscow: Nauka, 1974, p. 130.

    Google Scholar 

  15. Krstić, N.M., Lorenc, L.B., Pavlovizh, V.D., Kalvoda, J., Tinant, B., and Declercq, J-P., J. Chem. Res., Synop., 2002, p. 392.

  16. Odinokov, V.N., Bakeeva, R.S., Ishmuratov, G.Yu., and Tolstikov, G.A., Izv. Ross. Akad. Nauk, Ser. Khim., 1979, no. 8, p. 1912.

  17. Kagarlitskii, A.D., Adekenov, S.M., and Kupriyanov, A.N., Seskviterpenovye laktony rastenii Tsentral’nogo Kazakhstana (Sesquiterpene Lactones Isolated from Plants in the Central Kazakhstan Region), Alma-Ata: Nauka, 1987, p. 9.

    Google Scholar 

  18. Zielisska, K. and Kisiel, W., Phytochemistry, 2000, vol. 54, p. 791.

    Article  Google Scholar 

  19. Starcher, P.S. and Phillips, B., J. Am. Chem. Soc., 1958, vol. 80, p. 4079.

    Article  CAS  Google Scholar 

  20. Pradhan, B.P., Roy, A., and Patra, A., Indian J. Chem., Sect. B, 1992, vol. 31, p. 633.

    Google Scholar 

  21. Medvedeva, N.I., Flekhter, O.B., Tret’yakova, E.V., Galin, F.Z., Baltina, L.A., Spirikhin, L.V., and Tolstikov, G.A., Russ. J. Org. Chem., 2004, vol. 40, p. 1092.

    Article  CAS  Google Scholar 

  22. Organic Reactions in Steroid Chemistry, Fried, J. and Edwards, J.A., Eds., New York: Van Nostrand Reinhold, 1972, vol. 2.

    Google Scholar 

  23. Khalilova, A.Z., Litvinov, I.A., Beskrovnyi, D.V., Gubaidullin, A.T., Shakurova, E.R., Nuriev, I.F., Khalilov, L.M., and Dzhemilev, U.M., Khim. Prirodn. Soedin., 2004, p. 215.

Download references

Author information

Authors and Affiliations

  1. Institute of Petroleum Chemistry and Catalysis, Russian Academy of Sciences, pr. Oktyabrya 141, Ufa, 450075, Bashkortostan, Russia

    V. R. Akhmetova, E. R. Shakurova, A. Z. Khalilova, L. M. Khalilov & U. M. Dzhemilev

Authors
  1. V. R. Akhmetova
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. E. R. Shakurova
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. A. Z. Khalilova
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. L. M. Khalilov
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. U. M. Dzhemilev
    View author publications

    You can also search for this author in PubMed Google Scholar

Additional information

Original Russian Text © V.R. Akhmetova, E.R. Shakurova, A.Z. Khalilova, L.M. Khalilov, U.M. Dzhemilev, 2007, published in Zhurnal Organicheskoi Khimii, 2007, Vol. 43, No. 3, pp. 367–372.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Akhmetova, V.R., Shakurova, E.R., Khalilova, A.Z. et al. Synthesis and transformations of 20-oxo-30-nortaraxasteryl acetate derivatives. Russ J Org Chem 43, 363–369 (2007). https://doi.org/10.1134/S1070428007030050

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070428007030050

Keywords

Search

Navigation