Revisiting 23-iodospirostanes. New facts and full characterization

Steroids. 2009 Nov;74(12):996-1002. doi: 10.1016/j.steroids.2009.07.008. Epub 2009 Jul 29.

Abstract

In addition to a previous report, the reaction of tigogenin acetate with ICl in refluxing CHCl(3) produced the hitherto unknown 23R-iodotigogenin acetate, bearing an axial iodine atom at C-23 and its already reported 23S-epimer. The same treatment of sarsasapogenin acetate led to a single diasteromer characterized as 23S-iodosarsasapogenin acetate. A full characterization of the obtained compound including (1)H, (13)C NMR, MS and X-ray diffraction is provided.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Crystallography, X-Ray
  • Iodine / chemistry*
  • Magnetic Resonance Spectroscopy
  • Models, Molecular
  • Molecular Conformation
  • Spirostans / chemical synthesis*
  • Spirostans / chemistry*
  • Stereoisomerism

Substances

  • Spirostans
  • Iodine