Efficient Synthesis of Natural Polyphenolic Stilbenes: Resveratrol, Piceatannol and Oxyresveratrol

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概要

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• 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.

• 社団法人 日本薬学会の論文

著者

• Sun Hong-Yi

  Guangzhou Institute of Chemistry, Chinese Academy of Sciences

• Xiao Chun-Fen

  Guangzhou Institute of Chemistry, Chinese Academy of Sciences

• Cai Yu-Chen

  State Key Laboratory of Oncology in South China

• Chen Yu

  Guangzhou Institute of Chemistry, Chinese Academy of Sciences

• Wei Wen

  Guangzhou Institute of Chemistry, Chinese Academy of Sciences

• Liu Xian-Ke

  Guangzhou Institute of Chemistry, Chinese Academy of Sciences

• Lv Ze-Liang

  Guangzhou Institute of Chemistry, Chinese Academy of Sciences

• Zou Yong

  Guangzhou Institute of Chemistry, Chinese Academy of Sciences

関連論文

• Efficient Synthesis of Natural Polyphenolic Stilbenes: Resveratrol, Piceatannol and Oxyresveratrol
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