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
Article

Abstract

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.

Keywords

Stigmasterol Chromic Acid Methine Proton Enone Vinyl Proton 

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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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