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有机化学
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有机化学 ›› 2012, Vol. 32 ›› Issue (12): 2276-2282.DOI: 10.6023/cjoc201210016 上一篇    下一篇

研究论文

四个天然异戊烯基黄酮的全合成研究

左武标, 杨金会, 李红俊, 郭冬冬, 落俊山, 黄文倩   

  1. 宁夏大学天然气转化国家重点实验室培育基地 银川 750021
  • 收稿日期:2012-10-13 修回日期:2012-10-31 发布日期:2012-11-02
  • 通讯作者: 杨金会 E-mail:yang_jh@nxu.edu.cn
  • 基金资助:

    国家自然科学基金(Nos. 21162021, 20962016)、宁夏自然科学基金(No. NZ1006)、教育部“新世纪优秀人才支持计划资助”(No. NCET-09-0860)、国家重点基础研究发展计划(No. 2010CB534916)资助项目.

Study on Total Synthesis of Four Natural Prenylated Flavonoids

Zuo Wubiao, Yang Jinhui, Li Hongjun, Guo Dongdong, Luo Junshan, Huang Wenqian   

  1. State Key Laboratory Cultivation Base of Natural Gas Conversion, Ningxia University, Yinchuan 750021
  • Received:2012-10-13 Revised:2012-10-31 Published:2012-11-02
  • Supported by:

    Project supported by the National Natural Science Foundation of China (Nos. 21162021, 20962016), the Ningxia Natural Science Foundation (No. NZ1006), the Program for New Century Excellent Talents in University (No. NCET-09-0860) and the National Basic Research Program 973 of China (No. 2010CB534916).

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利用温和的方法进行了异戊烯基黄酮(±)-abyssinone-VI-4-O-methyl ether, (±)-abyssinone-IV-4'-O-methyl ether, (±)-abyssinone-V-4'-O-methyl ether和(±)-sigmoidin E的全合成研究, 同时通过对羟基苯甲醛的异戊烯基化以及在石油醚中低温结晶的方法合成了关键中间体4-羟基-3,5-二异戊烯基苯甲醛. 所有新化合物的结构都经过IR, 1H NMR, MS, HRMS确认.

关键词: 异戊烯基黄酮, (±)-abyssinone-VI-4-O-methyl ether, (±)-abyssinone-IV-4'-O-methyl ether, (±)-abyssinone- V-4'-O-methyl ether, (±)-sigmoidin E, 全合成

A facile approach for the total synthesis of prenylated flavonoids, (?)-abyssinone-VI-4-O-methyl ether (1), (?)-abyssinone-IV-4'-O-methyl ether (2), (?)-abyssinone-V-4'-O-methyl ether (3) and (?)-sigmoidin E (4), has been described. The key intermediate 4-hydroxy-3,5-di-(3-methylbut-2-enyl)benzaldehyde (6) was synthesized that features regioselective prenylation of 4-hydroxybenzaldehyde and crystallizing with petroleum ether from the reaction mixture by freeze-out effect. All structures of new compounds were confirmed by IR, 1H NMR, MS and HRMS techniques.

Key words: prenylated flavonoind, (?)-abyssinone-VI-4-O-methyl ether, (?)-abyssinone-IV-4'-O-methyl ether, (?)- abyssinone-V-4'-O-methyl ether, (?)-sigmoidin E, total synthesis