Structure elucidation of new compounds from acidic treatment of the progestins gestodene and drospirenone

Steroids. 2006 Aug;71(8):745-50. doi: 10.1016/j.steroids.2006.05.002.

Abstract

Gestodene acidic treatment afforded a single rearrangement product, namely 13-beta-ethyl-18,19-dinorpregna-4,14,16-trien-3,20-dione 3, which was originated through HCl-catalyzed Rupe rearrangement. Drospirenone acidic treatment yielded two epimeric lactones by addition of HCl to the 6beta,7beta-cyclopropane ring, namely 7beta-(chloromethyl)-15beta,16beta-methylene-3-oxo-17beta-pregn-4-ene-21,17-carbolactone 4 and 7beta-(chloromethyl)-15beta,16beta-methylene-3-oxo-17alpha-pregn-4-ene-21,17-carbolactone 5. The structure of the compounds was assessed by spectroscopic and crystallographic methods.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Androstenes / chemistry*
  • Crystallography, X-Ray
  • Models, Biological
  • Models, Molecular
  • Molecular Structure
  • Norpregnenes / chemistry*
  • Progesterone Congeners / chemical synthesis*

Substances

  • Androstenes
  • Norpregnenes
  • Progesterone Congeners
  • Gestodene
  • drospirenone