Transformed steroids

Communication 16. Wagner-Meerwein rearrangement of 16α, 17α-epoxypregn-5-ene-3β,20β-diol 3,20-diacetate under the conditions of the Grignard reaction
  • A. A. Akhrem
  • T. V. Ilyukhina
Organic and Biological Chemistry


  1. 1.

    The Wagner-Meerwein rearrangement of the starting oxide is observed when 16α,17α-epoxypregn-5-ene-3β,203-diol 3,20-diaeetate is reacted with methylmagnesium iodide.

  2. 2.

    The product of the indicated rearrangement is 18-nor-17β-methyl-17α-pregna-5,13 (14)-diene-3β, 16α,20β-triol.

  3. 3.

    It was discovered that the side chain of the steroidalβ-ketol is cleaved under alkaline conditions, which cleavage takes place by the retroaldol mechanism.



Oxide Steroid Iodide Diol Alkaline Condition 
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Copyright information

© Consultants Bureau 1969

Authors and Affiliations

  • A. A. Akhrem
    • 1
  • T. V. Ilyukhina
    • 1
  1. 1.N.D. Zelinskii Institute of Organic ChemistryAcademy of Sciences of the USSRUSSR

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