Synthesis of C-C-bridged bis-isoflavones

J Org Chem. 2000 Apr 21;65(8):2305-8. doi: 10.1021/jo991404g.

Abstract

Unique C-C-bridged bis-isoflavones 5, 8, and 9 were obtained by reaction of 2-bromomethyl-7,4'-dimethoxyisoflavone 4 with ethyl cyanoacetate anion or tetraethylammonium cyanide or by Pd-catalyzed ethoxycarbonylation, respectively. The phenolic carboxylic acid 7 is available from 5 in two steps.

Publication types

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

MeSH terms

  • Alkylation
  • Bridged-Ring Compounds / chemistry*
  • Carboxylic Acids / chemistry
  • Catalysis
  • Crystallography, X-Ray
  • Cyanides
  • Dimethyl Sulfoxide
  • Indicators and Reagents
  • Isoflavones / chemistry*
  • Lead
  • Oligopeptides / chemical synthesis
  • Oligopeptides / chemistry*

Substances

  • Bridged-Ring Compounds
  • Carboxylic Acids
  • Cyanides
  • Indicators and Reagents
  • Isoflavones
  • Oligopeptides
  • Lead
  • Dimethyl Sulfoxide