Three-step synthesis of flavanostilbenes with a 2-cyclohepten-1-one core by Cu-mediated[5+2]cycloaddition/decarboxylation cascade  

作　　者：Gangsheng Li Xiang Yuan Fu Liu Zhihua Liu Xujie Wang Yuanyuan Liu Yanmin Chen Tingting Wang Yanan Yang Peicheng Zhang 

机构地区：[1]State Key Laboratory of Bioactive Substance and Function of Natural Medicines,Institute of Materia Medica,Chinese Academy of Medical Sciences and Peking Union Medical College,Beijing 100050,China [2]Beijing Wehand-Bio Pharmaceutical Co.,Ltd.,Beijing 100500,China

出　　处：《Chinese Chemical Letters》2025年第2期350-355,共6页中国化学快报(英文版)

基　　金：financial surpport from the CAMS Innovation Fund for Medical Sciences(CIFMS,No.2021-I2M-1-028);supported by Biomedical High Performance Computing Platform,Chinese Academy of Medical Sciences。

摘　　要：The first synthesis of flavanostilbenes with a 2-cyclohepten-1-one core was carried out by applying an effective strategy in three steps from abundant polymerized flavanol resources.A key regio-and stereoselective Cu-mediated[5+2]cycloaddition/decarboxylation cascade was explored and applied without the use of protecting groups,and water as an environmentally friendly solvent contributed to the cascade.The intramolecular[5+2]cycloaddition mechanism,involving oxidation and dearomatization of the flavanol unit as a diene,was proposed and supported by the synthesis of the intermediate.The regioselectivity of the cyclization was found to be dependent on the substitution effects of the stilbene units by the exploration of substrate scope.

关 键 词：[5+2]Cycloaddition Biomimetic synthesis Copper Natural products SUBSTRATE 

分 类 号：O629[理学—有机化学]