Stereoselective halogenation of the 16-hydroxymethyl-3-methoxy-13alpha-estra-1,3,5(10)-trien-17-ols and their solvolytic investigation

Steroids. 2003 May;68(5):451-8. doi: 10.1016/s0039-128x(03)00048-5.

Abstract

The primary hydroxy functions of 16alpha-hydroxymethyl-3-methoxy-13alpha-estra-1,3,5(10)-trien-17beta-ol (3a) and 16beta-hydroxymethyl-3-methoxy-13alpha-estra-1,3,5(10)-trien-17alpha-ol (4a) were stereoselectively transformed into good leaving groups. On alkaline methanolysis of the 16-halomethyl or 16-tolylsulfonyloxymethyl derivatives, a new D-seco-13alpha-estrone derivative was obtained in high yield.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Bromine / chemistry
  • Chlorine / chemistry
  • Estriol / analogs & derivatives*
  • Estriol / chemical synthesis*
  • Estriol / chemistry
  • Halogens / chemistry*
  • Hydrocarbons, Halogenated / chemical synthesis
  • Hydrocarbons, Halogenated / chemistry
  • Iodine / chemistry
  • Models, Chemical
  • Solvents / chemistry*
  • Stereoisomerism
  • Structure-Activity Relationship

Substances

  • Halogens
  • Hydrocarbons, Halogenated
  • Solvents
  • estra-1,3,5(10)-triene-3,7,17-triol
  • Chlorine
  • Iodine
  • Estriol
  • Bromine