Synthesis of C17-OH-north unit of ritterazine G via "Red-Ox" modifications of hecogenin acetate

Steroids. 2013 Jul;78(7):639-43. doi: 10.1016/j.steroids.2013.02.015. Epub 2013 Mar 15.

Abstract

The C17-OH-north unit of ritterazine G was prepared in 13 steps from hecogenin acetate. This synthesis features a highly efficient and stereoselective introduction of the C17-OH via E-ring cleavage/F-ring formation, D-ring oxidation, and F-ring cleavage/E-ring formation.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • HeLa Cells
  • Humans
  • Molecular Structure
  • Oxidation-Reduction
  • Phenazines / chemical synthesis*
  • Phenazines / chemistry*
  • Spiro Compounds / chemistry*
  • Steroids / chemistry*

Substances

  • Phenazines
  • Spiro Compounds
  • Steroids
  • hecogenin acetate