Chemistry of Natural Compounds

, Volume 7, Issue 4, pp 481–485 | Cite as

Steroids XLIV. Synthesis and D-homoisomerization of 3β-acetoxy-6α-(N-acetylanilino)-17α-hydroxypregn-5-en-20-one

  • N. N. Suvorov
  • G. A. Frangulyan
  • V. L. Sadovskaya
  • L. M. Alekseeva
Article
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Summary

  1. 1.

    The reactions of 16β-bromo-3β,17α-dihydroxypregn-5-en-20-dione (III) and its 3,17-diacetate (IV) with aniline have been studied. The reaction of (III) with aniline leads to the formation of the 20-anil of 16α,17α-epoxypregnenolone (V) and the reaction of (IV) with aniline to the formation of 3-acetoxy-16α-(N-acetylanilino)-17α-hydroxypregn-5-en-20-one (IX).

     
  2. 2.

    The hydrolysis of the diacetate (IX) with potassium carbonate in aqueous methanol has been studied. The hydrolysis is accompanied by D-homoisomerization with the formation of 16α-anilino-3β,17α-dihydroxy-17β-methyl-D-homoandrost-5-en-17a-one.

     
  3. 3.

    The structures and configurations of the compounds obtained (V, VI, VII, IX, X, and XI) have been shown by a series of chemical transformations and by physicochemical methods.

     

Keywords

Aniline Hydroxy Group Diacetate Acetic Anhydride Potassium Carbonate 

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Copyright information

© Consultants Bureau, a division of Plenum Publishing Corporation 1973

Authors and Affiliations

  • N. N. Suvorov
  • G. A. Frangulyan
  • V. L. Sadovskaya
  • L. M. Alekseeva

There are no affiliations available

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