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有机化学
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有机化学 ›› 2011, Vol. 31 ›› Issue (08): 1230-1234. 上一篇    下一篇

研究论文

(±)-Glovanon和(±)-5-O-Methylglovanon的首次全合成及其抑菌活性研究

杨金会*,1，李红俊1，张玉恒1，江世智1，李云峰1，薛屏1，马玉龙2，刘万毅1,2   

  1. (1宁夏大学能源化工重点实验室 银川 750021)
    (2宁夏大学化学化工学院 银川 750021)
  • 收稿日期:2010-10-26 修回日期:2011-03-14 发布日期:2011-03-29
  • 通讯作者: 杨金会 E-mail:yang_jh@nxu.edu.cn

First Total Synthesis of (±)-Glovanon and (±)-5-O-Methylglovanon and Their Bacteriostatic Activity

Yang Jinhui*,1 Li Hongjun1 ZhangYu-heng1 Jiang Shizhi1 Li Yunfeng1 Xue Ping1 Ma Yulong2 Liu Wanyi1,2   

  1. (1 Key Laboratory of Energy Sources & Engineering, Ningxia University, Yinchuan 750021)
    (2 School of Chemistry and Chemical Engineering, Ningxia University, Yinchuan 750021)
  • Received:2010-10-26 Revised:2011-03-14 Published:2011-03-29

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以廉价的异香草醛和2,4,6-三羟基苯乙酮为起始原料, 经过C-异戊烯基化、选择性甲基化、甲氧甲基化、羟醛缩合、去保护基、催化环化以及脱除甲基等步骤, 分别以13.3%和23%的总收率首次完成了天然异戊烯基黄烷酮Glovanon (1)和5-O-methylglovanon (2)的全合成．合成的关键步骤是2,4,6-三羟基苯乙酮的单C-异戊烯基化. 所有新化合物的结构都经过1H NMR, IR, MS确认. 抑菌活性研究表明, 两种新合成的化合物对藤黄微球菌(M. luteus)和大肠杆菌(E. coli)均有良好的抑制作用.

关键词: glovanon, 5-O-methylglovanon, 黄烷酮, 异戊烯基黄烷酮, 全合成, 抑菌活性

The total synthesis of glovanon (1) and 5-O-methylglovanon (2), two naturally occurring isoprenylflavanoids, was first achieved through C-prenylation, selective methylation or methoxymethyl protection, aldol condensation, deprotection, cyclization and demethylation starting from cheap isovanillin and 2,4,6-trihydroxyacetophenone with total yields of 23% and 13.3%, respectively. The key step was C-prenylation of 2,4,6-trihydroxyacetophenone. The structures of all new componds were confirmed by 1H NMR, IR and MS techniques, and the bioassay results indicated that the two novelly synthesized compounds demonstrated good inhibitory effect against Micrococcus luteus (M. luteus) and Escherichia coli (E. coli).

Key words: glovanon, 5-O-methylglovanon, flavanoid, isoprenylflavanoid, total synthesis, bacteriostatic activity