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Chin. J. Org. Chem. ›› 2010, Vol. 30 ›› Issue (10): 1574-1579. Previous Articles     Next Articles

Notes

氧化白藜芦醇的合成

孙洪宜1,2，肖春芬1,2，魏文1，陈煜1,2，吕泽良1,2,3，邹永*,1   

  1. (1中国科学院广州化学研究所 广州 510650)
    (2中国科学院研究生院 北京 100049)
    (3曲靖师范学院化学化工学院 曲靖 655011)
  • 收稿日期:2009-12-19 修回日期:2010-03-31 发布日期:2010-05-25
  • 通讯作者: 孙洪宜 E-mail:sunhy85@hotmail.com
  • 基金资助:

    广东省中国科学院战略合作;广州市科技计划

Synthesis of Oxyresveratrol

Sun Hongyi1,2 Xiao Chunfen1,2 Wei Wen1 Chen Yu1,2 Lü Zeliang1,2,3 Zou Yong*,1   

  1. (1 Guangzhou Institute of Chemistry, Chinese Academy of Science, Guangzhou 510650)
    (2 Graduate School of Chinese Academy of Sciences, Beijing 100049)
    (3 Department of Chemistry and Chemical Engineering, Qujing Normal University, Qujing 655011)
  • Received:2009-12-19 Revised:2010-03-31 Published:2010-05-25

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A convenient method for the practical synthesis of oxyresveratrol is described. Starting from the readily available 3,5-dihydroxyacetophenone (1), 3,5-dimethoxyphenylacetic acid (3) can be achieved through methylation and Willgerodt-Kindler rearrangement. Perkin condensation between 3 and 2,4-dimethoxy- benzaldehyde (4) formed the stilbene skeleton, and by subsequent decarboxylation and demethylation/isomerization process, oxyresveratrol (7) was obtained in an overall yield of 30%. The synthetic method has several advantages such as mild reaction conditions, high yield of product and simple operations. The structures of the target compound and key intermediates were verified by MS, IR, 1H NMR and 13C NMR techniques.

Key words: oxyresveratrol, phenylacetic acid, Willgerodt-Kindler rearrangement, methylation, Perkin reaction, decarboxylation, demethylation