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

Chin. J. Org. Chem. ›› 2011, Vol. 31 ›› Issue (08): 1230-1234. Previous Articles Next Articles

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(±)-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 Wanyi^1,2

(¹Key Laboratory of Energy Sources & Engineering, Ningxia University, Yinchuan 750021)
(²School of Chemistry and Chemical Engineering, Ningxia University, Yinchuan 750021)

Received:2010-10-26 Revised:2011-03-14 Published:2011-03-29

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

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YANG Jin-Hui, LI Hong-Jun, ZHANG Yu-Heng, JIANG Shi-Zhi, LI Yun-Feng, XUE Ping, MA Yu-Long, LIU Wan-Yi. First Total Synthesis of (±)-Glovanon and (±)-5-O-Methylglovanon and Their Bacteriostatic Activity[J]. Chin. J. Org. Chem., 2011, 31(08): 1230-1234.

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

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

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