Synthesis of novel structurally simplified estrogen analogues

Chemistry. 2008;14(12):3670-9. doi: 10.1002/chem.200701600.

Abstract

A library of 17 novel estrogen analogues 3 and 4 containing different substituents at rings A and D (steroid nomenclature) was prepared in a five- to seven-step synthesis. The key transformation is a Sonogashira-coupling of cyclic vinyl iodides of type 7 or 8 with phenylacetylenes of type 9. Reduction of the keto function in 3 led to the estradiol analogue 5.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Estradiol / analogs & derivatives*
  • Estradiol / chemical synthesis*
  • Estradiol / chemistry
  • Estrone / analogs & derivatives*
  • Estrone / chemical synthesis*
  • Estrone / chemistry
  • Molecular Conformation
  • Small Molecule Libraries / chemical synthesis*
  • Stereoisomerism

Substances

  • Small Molecule Libraries
  • Estrone
  • Estradiol