Skip to main content
Log in

Convenient synthesis of drimenol and its oxidation with selenium dioxide

  • Published:
Russian Chemical Bulletin Aims and scope

Abstract

A convenient synthesis of drimenol by treatment of readily available drimane-8α, 11-diol 11-monoacetate with sulfuric acid in ethanol under mild conditions was developed. Oxidation of drimenol with selenium dioxide gives known drim-7-ene-9α, 11-diol and drim-7-ene-11,12-diol as the major products.

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

Access this article

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

Instant access to the full article PDF.

Similar content being viewed by others

References

  1. B. J. M. Jansen and A. de Groot, Nat. Prod. Rep., 1991, 8, 319.

    Article  CAS  Google Scholar 

  2. J. Lopez, J. Sierra, and M. Cortes, Chem. Lett., 1986, 2073.

  3. M. Cortes, I. Razmilic, and J. Lopez, J. Nat. Prod., 1990, 53, 1369.

    Article  CAS  Google Scholar 

  4. A. F. Barrero, M. Cortes, E. A. Manzaneda, E. Cabrera, R. Chahboun, M. Lara, and A. R. Rivas, J. Nat. Prod., 1999, 62, 1488.

    Article  CAS  PubMed  Google Scholar 

  5. B. J. M. Jansen and A. de Groot, Nat. Prod. Rep., 1991, 8, 309.

    Article  CAS  PubMed  Google Scholar 

  6. M. Toyota, Y. Ooiso, T. Kusuyama, and Y. Asakawa, Phytochemistry, 1994, 35, 1263.

    Article  CAS  Google Scholar 

  7. B. P. Ying, G. Paiser, I. I. Ji, K. Mathias, D. Tutko, and Y. S. Hwang, Phytochemistry, 1995, 38, 909.

    Article  CAS  Google Scholar 

  8. A. F. Barrero, E. A. Manzaneda, J. Altarejos, S. Salido, J. M. Ramos, M. S. J. Simmonds, and W. M. Blaney, Tetrahedron, 1995, 51, 7435.

    Article  CAS  Google Scholar 

  9. B. M. F. Lagnel, Ch. Morin, and A. de Groot, Synthesis, 2000, 1907.

  10. K. I. Kuchkova, Y. M. Chumakov, Y. A. Simonov, G. Bocelli, A. A. Panasenko, and P. F. Vlad, Synthesis, 1997, 1045.

  11. P. F. Vlad, M. N. Koltsa, and G. N. Mironov, Izv. Akad. Nauk, Ser. Khim., 1997, 896 [Russ. Chem. Bull., 1997, 46, 855 (Engl. Transl.)].

    Google Scholar 

  12. S. Poigny, T. Huor, M. Guyot, and M. Samadi, J. Org. Chem., 1999, 64, 9318.

    Article  CAS  Google Scholar 

  13. P. F. Vlad, G. V. Kryshtal’, and G. V. Lazur’evskii, Zh. Obshch. Khim., 1967, 37, 2187 [J. Gen. Chem. USSR, 1967, 37 (Engl. Transl.)].

    CAS  Google Scholar 

  14. I. Razmilic, J. Lopez, and M. Cortes, Synth. Commun., 1993, 23, 1155.

    CAS  Google Scholar 

  15. K. Mori and H. Watanabe, Tetrahedron, 1986, 42, 273.

    Article  CAS  Google Scholar 

  16. G. D. Brown, Phytochemistry, 1994, 35, 975.

    Article  CAS  Google Scholar 

  17. J. G. Urones, J. S. Marcos, B. G. Perez, D. Diez, A. M. Lithgow, P. M. Gomes, P. Basabe, and N. M. Garrido, Tetrahedron, 1994, 50, 10995.

    Article  CAS  Google Scholar 

  18. M. L. Oyarzun, M. Cortes, and J. Sierra, Synth. Commun., 1982, 12, 951.

    CAS  Google Scholar 

  19. I. Razmilic, J. Lopez, J. Sierra, and M. Cortes, Synth. Commun., 1987, 17, 95.

    CAS  Google Scholar 

  20. D. M. Hollinshead, S. C. Howell, S. V. Ley, M. Mahon, N. M. Ratcliffe, and P. A. Worthington, J. Chem. Soc., Perkin Trans. 1, 1983, 1579.

  21. H. H. Appel, C. J. W. Brooks, and K. H. Overton, J. Chem. Soc., 1959, 3322.

Download references

Author information

Authors and Affiliations

Authors

Additional information

__________

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 12, pp. 2745–2748, December, 2004.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Kuchkova, K.I., Aricu, A.N., Dragalin, I.P. et al. Convenient synthesis of drimenol and its oxidation with selenium dioxide. Russ Chem Bull 53, 2862–2865 (2004). https://doi.org/10.1007/s11172-005-0203-x

Download citation

  • Received:

  • Revised:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11172-005-0203-x

Key words

Navigation