Stereoselective synthesis of pentacyclic steroids functionalized at C-11

Steroids. 2012 Sep;77(11):1092-100. doi: 10.1016/j.steroids.2012.04.004. Epub 2012 Apr 26.

Abstract

We set out to describe an efficient and versatile method for preparing pentacyclic steroids diversely substituted at C-11 from cholic acid, via a stereoselective epoxidation and the epoxide opening as the key steps. The characteristic (1)H and (13)C NMR spectroscopic features of the synthesized compounds are reported.

MeSH terms

  • Amines / chemistry
  • Cholic Acid / chemistry
  • Epoxy Compounds / chemistry
  • Lactones / chemistry
  • Magnetic Resonance Spectroscopy
  • Molecular Structure
  • Stereoisomerism
  • Steroids / chemical synthesis*
  • Sulfhydryl Compounds / chemistry
  • Sulfones / chemistry

Substances

  • Amines
  • Epoxy Compounds
  • Lactones
  • Steroids
  • Sulfhydryl Compounds
  • Sulfones
  • Cholic Acid