白花前胡素E的全合成研究  

Total Synthesis of Praeruptorin E

作　　者：白磊阳 付蓓 刘海平 淳享 姜雪峰 Leiyang Bai;Bei Fu;Haiping Liu;Xiang Chun;Xuefeng Jiang(School of Chemistry and Molecular Engineering,Shanghai Key Laboratory of Green Chemistry and Chemical Progress,East China Normal University,Shanghai 200062)

机构地区：[1]华东师范大学化学与分子工程学院、上海市绿色化学与化工过程绿色化重点实验室,上海200062

出　　处：《有机化学》2025年第3期1009-1020,共12页Chinese Journal of Organic Chemistry

基　　金：基金资助:国家自然科学基金(22125103);上海市基础研究领域项目(22JC1401000);中国博士后科学基金(2023M731094);中国博士后科学基金(BX20230127)。

摘　　要：白花前胡素E (Praeruptorin E)拥有特异而多样的生物活性, 但合成路线尚未见报道, 严重限制了其药物发现与药物研究. 结构剖析表明该分子的合成存在四大难题: 对映选择性、化学选择性、区域选择性以及Z/E选择性. 以商业易得的3-甲基-2-丁烯醛和原甲酸三乙酯为原料, 经5到7步反应实现了白花前胡素E的不对称全合成, 并且发散式建立了8个白花前胡素E类似物库, 为其活性研究及药物筛选奠定了优质的合成基础.Praeruptorin E expresses specific and diverse biological activities but with no synthetic report, which dramatically limits its medicinal research. Structural analysis reveals that there are four major challenges in the synthesis of this nature product: enantioselectivity, chemoselectivity, regioselectivity, and Z/E selectivity. Herein, the first asymmetric total synthesis of praeruptorin E was achieved through five/seven steps, utilizing commercially available 3-methyl-2-butenal and triethyl orthoformate as raw materials. Additionally, a eight-membered library of praeruptorin E analogs has also been established via this strategy, laying a solid foundation for its activity test and drug discovery.

关 键 词：白花前胡素E 对映选择性 化学选择性 区域选择性 Z/E选择性 

分 类 号：O626[理学—有机化学]