Efficient synthesis of natural polyphenolic stilbenes: resveratrol, piceatannol and oxyresveratrol

Chem Pharm Bull (Tokyo). 2010 Nov;58(11):1492-6. doi: 10.1248/cpb.58.1492.

Abstract

The practical synthesis of important natural polyphenolic stilbenes, including resveratrol, piceatannol and oxyresveratrol, through Perkin methodology is described. Starting from 3,5-dihydoxyacetophenone (1), the common intermediate 3,5-dimethoxyphenylacetic acid (3) can be obtained via methylation and Willgerodt-Kindler reaction. Perkin condensations between (3) and substituted phenylaldehydes 4 furnished E-2,3-diarylacrylic acids 5, followed by decarboxylation in Cu/quinoline giving stilbene intermediates 6 which bear the Z-configuration. Finally, through a simultaneous demethylation/isomerization process in AlI₃/CH₃CN system, the target compounds 7a-c can be obtained respectively in good to high overall yields. The synthetic method proved to be more concise, trans-specific, mild, economical and commonly applicable.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antineoplastic Agents, Phytogenic / chemical synthesis*
  • Antineoplastic Agents, Phytogenic / chemistry
  • Antioxidants / chemical synthesis*
  • Antioxidants / chemistry
  • Fallopia japonica / chemistry
  • Flavonoids / chemical synthesis
  • Flavonoids / chemistry
  • Molecular Structure
  • Moraceae / chemistry
  • Phenols / chemical synthesis
  • Phenols / chemistry
  • Plant Extracts / chemical synthesis*
  • Plant Extracts / chemistry
  • Plants / chemistry*
  • Polyphenols
  • Protein-Tyrosine Kinases / antagonists & inhibitors*
  • Resveratrol
  • Stilbenes / chemical synthesis*
  • Stilbenes / chemistry

Substances

  • Antineoplastic Agents, Phytogenic
  • Antioxidants
  • Flavonoids
  • Phenols
  • Plant Extracts
  • Polyphenols
  • Stilbenes
  • puag-haad
  • 3,3',4,5'-tetrahydroxystilbene
  • Protein-Tyrosine Kinases
  • Resveratrol