The flavan-isoflavan rearrangement: bioinspired synthetic access to isoflavonoids via 1,2-shift-alkylation sequence

Chem Commun (Camb). 2015 Apr 25;51(32):7012-4. doi: 10.1039/c5cc01572c. Epub 2015 Mar 24.

Abstract

An approach to 2-substituted isoflavonoids is reported based on the 1,2-shift of the aryl group in the catechin skeleton followed by the in situ alkylation. Synthesis of (-)-equol, a natural isoflavan with estrogenic activities, was achieved.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkylation
  • Biomimetics*
  • Chemistry Techniques, Synthetic
  • Flavins / chemistry*
  • Isoflavones / chemical synthesis*
  • Isoflavones / chemistry*

Substances

  • Flavins
  • Isoflavones