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高等学校化学研究 ›› 2012, Vol. 28 ›› Issue (4): 631-636.

• Articles • 上一篇    下一篇

Synthesis of Bioactive Natural Polymethoxyflavones and Their Vinyl Ether Derivatives

CAI Shuang-lian, LIU Shuang, LIU Li, WANG Qiu-an   

  1. College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082, P. R. China
  • 收稿日期:2011-11-28 修回日期:2012-01-11 出版日期:2012-07-25 发布日期:2012-07-25
  • 通讯作者: WANG Qiu-an E-mail:WangQA@hnu.edu.cn
  • 基金资助:

    Supported by the Science & Technology Planning Project of Hunan Province, China (No.2011FJ3214).

Synthesis of Bioactive Natural Polymethoxyflavones and Their Vinyl Ether Derivatives

CAI Shuang-lian, LIU Shuang, LIU Li, WANG Qiu-an   

  1. College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082, P. R. China
  • Received:2011-11-28 Revised:2012-01-11 Online:2012-07-25 Published:2012-07-25
  • Supported by:

    Supported by the Science & Technology Planning Project of Hunan Province, China (No.2011FJ3214).

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摘要： Bioactive natural polymethoxyflavones 1-6 and their vinyl ether derivatives 7-15 were synthesized by bromination, aromatic nucleophilic substitution, methylation, benzyl protection, Friedel-Crafts acetylation, aldol condensation, cyclization, DDQ dehydrogenation, regioselective demethylation, debenzylation and O-prenylation or O-farnesylation with resorcinol and appropriate substituted benzaldehydes as starting materials. Among them, compounds 7-15 are new compounds. Natural products 2-4 were firstly total synthesized. The syntheses of compounds 1, 5 and 6 were efficiently improved by the new synthetic routes. The structures of all synthetic compounds were confirmed by NMR, IR spectra and MS.

关键词: Flavonoid, Polymethoxyflavone, Prenylation, Farnesylation

Abstract: Bioactive natural polymethoxyflavones 1-6 and their vinyl ether derivatives 7-15 were synthesized by bromination, aromatic nucleophilic substitution, methylation, benzyl protection, Friedel-Crafts acetylation, aldol condensation, cyclization, DDQ dehydrogenation, regioselective demethylation, debenzylation and O-prenylation or O-farnesylation with resorcinol and appropriate substituted benzaldehydes as starting materials. Among them, compounds 7-15 are new compounds. Natural products 2-4 were firstly total synthesized. The syntheses of compounds 1, 5 and 6 were efficiently improved by the new synthetic routes. The structures of all synthetic compounds were confirmed by NMR, IR spectra and MS.

Key words: Flavonoid, Polymethoxyflavone, Prenylation, Farnesylation