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Russian Journal of Organic Chemistry

, Volume 42, Issue 1, pp 36–41 | Cite as

Synthetic transformations of higher terpenoids: XII. Transformation of lambertianic acid into 14,16-epoxyabietane diterpenoids

  • S. V. Chernov
  • E. E. Shul’ts
  • M. M. Shakirov
  • G. A. Tolstikov
Article

Abstract

Hydroxylation of lambertianic acid with potassium permanganate in alkaline medium afforded 15,16-epoxy-8α,17-dihydroxy-13(16),14-labdadienoic acid which was oxidized with periodic acid to the corresponding 8α-hydroxy aldehyde, and the latter underwent smooth cyclization in acid medium to give diterpenoid of the 14,16-epoxyabietane series.

Keywords

Potassium Organic Chemistry Aldehyde Acid Medium Alkaline Medium 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

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References

  1. 1.
    Kharitonov, Yu.V., Shul’ts, E.E., Shakirov, M.M., and Tolstikov, G.A., Russ. J. Org. Chem., 2005, vol. 41, p. 1145.CrossRefGoogle Scholar
  2. 2.
    Faulkner, D.J., Nat. Prod. Rep., 2002, vol. 19, no. 1, p. 1.Google Scholar
  3. 3.
    Hson Mou Chang, Kwok Ping Cheng, Tai Francis Choang, Hak Fun Chow, Kuk Ying Chui, Po Ming Hon, Fan Wah Lau Tan, Yun Yang, Zeng Pei Zhong, Chi Ming Lee, Hing Leung Sham, Chun Fei Chan, Yu Xin Cui, and Wong, H.N.C., J. Org. Chem., 1990, vol. 55, p. 3537.Google Scholar
  4. 4.
    Thomson, R.H., Naturally Occuring Quinones IV: Recent Advances, London: Blackie Academic & Professional, 1997, 4th ed., p. 694.Google Scholar
  5. 5.
    Lee, J. and Snyder, J.K., J. Org. Chem., 1992, vol. 57, p. 5301.Google Scholar
  6. 6.
    Gustafson, K., Andersen, R.J., He, C.H., and Clardy, J., Tetrahedron Lett., 1985, vol. 26, p. 2521.CrossRefGoogle Scholar
  7. 7.
    Faulkner, D.J., Molinski, T.F., Andersen, R.J., Dumdei, E.J., and Dilip de Silva E., Comp. Biochem. Physiol., Part C: Pharmacol., Toxicol., Endocrinol., 1990, vol. 97, no. 2, p. 233.Google Scholar
  8. 8.
    Dumdei, E.J., Kubanek, J., Coleman, J.E., Pika, J., Andersen, R.J., Steiner, J.R., and Clardy, J., Can. J. Chem., 1997, vol. 75, p. 773.Google Scholar
  9. 9.
    Chernov, S.V., Shults, E.E., Shakirov, M.M., Bagrjanskaja, I.Yu., Gatilov, Yu.V., and Tolstikov, G.A., Arkivoc, 2003, part XIII, p. 172.Google Scholar
  10. 10.
    Steiger, M. and Reichstein, T., Helv. Chim. Acta, 1938, vol. 21, p. 546.Google Scholar
  11. 11.
    Vlad, P.F. and Ungur, N.D., Khim. Prirodn. Soedin., 1984, no. 6, p. 725.Google Scholar

Copyright information

© Pleiades Publishing, Inc. 2006

Authors and Affiliations

  • S. V. Chernov
    • 1
  • E. E. Shul’ts
    • 1
  • M. M. Shakirov
    • 1
  • G. A. Tolstikov
    • 1
  1. 1.Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian DivisionRussian Academy of SciencesNovosibirskRussia

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