四个天然异戊烯基黄酮的全合成研究有机化学.pdfVIP

DOI: 10.6023/cjoc201210016 研究论文 有机化学 Chinese Journal of Organic Chemistry ARTICLE 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 (宁夏大学天然气转化国家重点实验室培育基地 银川 750021) 摘要 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 Study on Total Synthesis of Four Natural Prenylated Flavonoids Zuo, Wubiao Yang, Jinhui* Li, Hongjun Guo, Dongdong Luo, Junshan Huang, Wenqian (State Key Laboratory Cultivation Base of Natural Gas Conversion, Ningxia University, Yinchuan 750021) Abstract 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 de- scribed. The key intermediate 4-hydroxy-3,5-di-(3-methylbut-2-enyl)benzaldehyde (6) was synthesized that features regiose- lective 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. Keywords prenylated flavon