白花前胡素E的全合成研究

doi:10.6023/cjoc202407003

研究论文

白花前胡素E的全合成研究

白磊阳^a, 付蓓^a, 刘海平^a, 淳享^a, 姜雪峰^a,*

^a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

收稿日期:2024-07-02 修回日期:2024-08-14
基金资助:
国家自然科学基金(No. 22125103),上海市基础研究领域项目(No. 22JC1401000)和中国博士后科学基金(No. 2023M731094, BX20230127)资助项目.

Total synthesis of Praeruptorin E

Bai Leiyang^a, Fu Bei^a, Liu Haiping^a, Chun Xiang^a, Jiang Xuefeng^a,*

^aSchool of Chemistry and Molecular Engineering, Shanghai Key Laboratory of Green Chemistry and Chemical Progress, East China Normal University, Shanghai 200062, China

Received:2024-07-02 Revised:2024-08-14
Contact: *E-mail: xfjiang@chem.ecnu.edu.cn
Supported by:
NSFC (22125103), the STCSM (22JC1401000), and the China Postdoctoral Science Foundation (2023M731094 and BX20230127).

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摘要/Abstract

白花前胡素E (Praeruptorin E) 拥有特异而多样的生物活性,但合成路线尚无报道,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。本文以商业易得的3-甲基-2-丁烯醛和原甲酸三乙酯为原料,经五到七步反应实现了白花前胡素E的首次不对称全合成,并且发散式建立了八个白花前胡素E类似物库,为其活性研究及药物筛选奠定了优质合成基础。

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

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 synthesis of this nature product: enantioselectivity, chemoselectivity, regioselectivity, and Z/E selectivity. Herein, we achieved the first asymmetric total synthesis of Praeruptorin E 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.

Key words: Praeruptorin E, Enantioselectivity, Chemoselectivity, Regioselectivity, Z/E selectivity

引用此文

白磊阳, 付蓓, 刘海平, 淳享, 姜雪峰. 白花前胡素E的全合成研究[J]. 有机化学, doi: 10.6023/cjoc202407003.

Bai Leiyang, Fu Bei, Liu Haiping, Chun Xiang, Jiang Xuefeng. Total synthesis of Praeruptorin E[J]. Chinese Journal of Organic Chemistry, doi: 10.6023/cjoc202407003.

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