The stereochemistry of the Grignard reaction of steroidal 4,5-epoxy-3-ketones

Uyanik C. , Malay A., Ayna A., Hanson J., Hitchcock P.

STEROIDS, vol.70, no.2, pp.71-75, 2005 (Journal Indexed in SCI) identifier identifier identifier

  • Publication Type: Article / Article
  • Volume: 70 Issue: 2
  • Publication Date: 2005
  • Doi Number: 10.1016/j.steroids.2004.09.002
  • Title of Journal : STEROIDS
  • Page Numbers: pp.71-75


The stereochemistry of the addition of methylmagnesium bromide to a steroidal 4,5-epoxy-3-ketone has been shown to be determined by the stereochemistry of the epoxide. The epoxidation to the corresponding 3-alkyl-3-hydroxy-4-enes by per-acid was determined by the stereochemistry of the allylic alcohol. (C) 2004 Elsevier Inc. All rights reserved.