Transformed steroids. Communication 5. Opening of 5,6- and 20, 21-epoxide rings in steroids by fluorine-containing agents

  • I. G. Reshetova
  • A. A. Akhrem
Organic and Biological Chemistry

Summary

  1. 1.

    For the case of 5α,6α:20ξ,21-diepoxypregnane-3β,17β-diol 3-acetate (I) a study of the reactivity of the epoxide rings toward various fluorine-containing agents and the stereochemistry of their decyclization.

     
  2. 2.

    On the basis of work with the 5α,6α:20ξ,21-diepoxide (I) a method was developed for the simultaneous introduction of two fluorine atoms in the 6- and 20-positions of steroids of the pregnane series.

     
  3. 3.

    20ν,21-Epoxy-6β-fluoropregnane-3β,5α,17β-triol 3-acetate (II) was converted into the Δ4-3-keto steroid (X), an intermediate product in the synthesis of 6α-fluorocortexolone and 6α-fluoroprogesterone.

     
  4. 4.

    From an examination of the behavior of (I), (II), and (VI), which contain a 17β-hydroxy-20ξ,21-epoxide grouping, it was shown that in a strongly alkaline medium the 20ξ,21-epoxide grouping migrates with formation of 5α,6α:17β,20-diepoxypregnane-3β,21-diol (VII).

     

Keywords

Steroid Fluorine Epoxide Diol Intermediate Product 

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Copyright information

© Consultants Bureau Enterprises Inc. 1965

Authors and Affiliations

  • I. G. Reshetova
    • 1
  • A. A. Akhrem
    • 1
  1. 1.N. D. Zelinskii Institute of Organic ChemistryAcademy of SciencesUSSR

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