Facile synthesis of novel D-ring modified steroidal dienamides via rearrangement of 2H-pyrans

Steroids. 2013 May;78(5):494-9. doi: 10.1016/j.steroids.2013.02.004. Epub 2013 Feb 24.

Abstract

A simple and practical method for synthesis of the D-ring modified steroidal dienamides (4a-k) from the steroidal α,α-dicyanoalkene 3 and aldehydes via vinylogous aldol reaction was first reported. By using NaOAc as a base, the desired products were obtained in moderate to good yields in ethanol under mild conditions. All the synthesized steroidal dienamides are new and are currently being evaluated for their biological activities.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aldehydes / chemistry
  • Alkenes / chemistry*
  • Chemistry Techniques, Synthetic
  • Pyrans / chemistry*
  • Steroids / chemical synthesis*
  • Steroids / chemistry*

Substances

  • Aldehydes
  • Alkenes
  • Pyrans
  • Steroids