Chemistry of Natural Compounds

, Volume 28, Issue 6, pp 579–583 | Cite as

Synthesis of 3α-hydroxy-6-ketobrassinosteroids

  • N. V. Kovganko
  • O. P. Kananovich
  • S. K. Ananich


The synthesis has been effected of the new brassinosteroids (22S,23S)-28-homotyphasterol, 24-epityphasterol, and (22S,23S)-24-epityphasterol, which belong to the 3α-hydroxy-6-oxosteroids. For obtaining (22S,23S)-28-homotyphasterol from stigmasterol, a new scheme of synthesis has been developed the key stages of which are the reduction of a 2α,3α-epoxy-6-ketone with lithium tetrahydroaluminate and the selective oxidation of the resulting 3α,6β-diol to the 3α-hydroxy-6-ketone.


Stigmasterol Chromic Acid Methine Proton Enone Vinyl Proton 


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Literature cited

  1. 1.
    N. V. Kovganko, Khim. Prir. Soedin., No. 2, 159–172 (1991).Google Scholar
  2. 2.
    J. A. Schneider, K. Yoshihara, and K. Nakanishi, Tetrahedron Lett.,24, 3859–3860 (1983).CrossRefGoogle Scholar
  3. 3.
    T Yokota, M. Arima, N. Takahashi, S. Takatsuto, N. Ikekawa, and T. Takematsu, Agr. Biol. Chem.,47, 2419–2420 (1983).Google Scholar
  4. 4.
    N. V. Kovganko and Zh. N. Kashkan, Khim. Prir. Soedin., 771–776 (1990).Google Scholar
  5. 5.
    N. V. Kovganko and S. K. Ananich, Khim. Prir. Soedin., 728 (1992), [in this issue].Google Scholar
  6. 6.
    N. V. Kovganko and Zh. N. Kashkan, Zh. Prir. Khim.,26, No. 12, 2545–2552 (1990).Google Scholar
  7. 7.
    A. A. Akhrem, F. A. Lakhvich, V. A. Khrpiach, V. N. Zhabinskii, and N. V. Kovganko, Dokl. Akad. Nauk SSSR,275, No. 5, 1089–1091 (1984).Google Scholar

Copyright information

© Plenum Publishing Corporation 1993

Authors and Affiliations

  • N. V. Kovganko
  • O. P. Kananovich
  • S. K. Ananich

There are no affiliations available

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