Chinese Journal of Organic Chemistry >
Total Synthesis of Praeruptorin E
Received date: 2024-07-02
Revised date: 2024-08-14
Online published: 2024-09-30
Supported by
National Natural Science Foundation of China(22125103); Shanghai Municipal Major Basic Research Project(22JC1401000); China Postdoctoral Science Foundation(2023M731094); China Postdoctoral Science Foundation(BX20230127)
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.
Leiyang Bai , Bei Fu , Haiping Liu , Xiang Chun , Xuefeng Jiang . Total Synthesis of Praeruptorin E[J]. Chinese Journal of Organic Chemistry, 2025 , 45(3) : 1009 -1020 . DOI: 10.6023/cjoc202407003
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