Total synthesis of (S)-equol

Org Lett. 2006 Nov 23;8(24):5441-3. doi: 10.1021/ol0620444.

Abstract

The first enantioselective total synthesis of (S)-equol is reported. The described route relies on an Evans alkylation to form the stereocenter and an intramolecular Buchwald etherification to generate the chroman ring. Key features of this method include its brevity, its scalability, and the low cost of starting materials. [reaction: see text].

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Alkylation
  • Chromans / chemical synthesis
  • Chromatography, High Pressure Liquid
  • Equol
  • Ethers / chemical synthesis
  • Indicators and Reagents
  • Isoflavones / chemical synthesis*
  • Stereoisomerism

Substances

  • 4',7-dihydroxy-3,4-dihydroisoflavone
  • Chromans
  • Ethers
  • Indicators and Reagents
  • Isoflavones
  • Equol