Potassium Hexacyanoferrate (III)-Catalyzed Dimerization of Hydroxystilbene: Biomimetic Synthesis of Indane Stilbene Dimers

Molecules. 2015 Dec 18;20(12):22662-73. doi: 10.3390/molecules201219872.

Abstract

Using potassium hexacyanoferrate (III)-sodium acetate as oxidant, the oxidative coupling reaction of isorhapontigenin and resveratrol in aqueous acetone resulted in the isolation of three new indane dimers 4, 6, and 7, together with six known stilbene dimers. Indane dimer 5 was obtained for the first time by direct transformation from isorhapontigenin. The structures and relative configurations of the dimers were elucidated using spectral analysis, and their possible formation mechanisms were discussed. The results indicate that this reaction could be used as a convenient method for the semi-synthesis of indane dimers because of the mild conditions and simple reaction products.

Keywords: biomimetic synthesis; hydroxystilbene; indane stilbene dimer; potassium hexacyanoferrate (III).

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Biomimetics
  • Catalysis
  • Dimerization
  • Ferricyanides / chemistry*
  • Indans / chemical synthesis*
  • Oxidation-Reduction
  • Resveratrol
  • Sodium Acetate / chemistry
  • Stilbenes / chemical synthesis*
  • Stilbenes / chemistry

Substances

  • Ferricyanides
  • Indans
  • Stilbenes
  • Sodium Acetate
  • Resveratrol
  • potassium ferricyanide