Highly stereoselective construction of polycyclic benzofused tropane scaffolds and their latent bioactivities: bifunctional phosphonium salt-enabled cyclodearomatization process

作     者：Jian-Ping Tan Xiaojie Li Yuan Chen Xianle Rong Lixiang Zhu Chunhui Jiang Kai Xiao Tianli Wang Jian-Ping Tan;Xiaojie Li;Yuan Chen;Xianle Rong;Lixiang Zhu;Chunhui Jiang;Kai Xiao;Tianli Wang

作者机构：Key Laboratory of Green Chemistry&TechnologyMinistry of EducationCollege of ChemistrySichuan UniversityChengdu 610064China National Chengdu Center for Safety Evaluation of Drugs and National Clinical Research Center for GeriatricsWest China HospitalSichuan UniversityChengdu 610064China School of Environmental and Chemical EngineeringJiangsu University of Science and TechnologyZhenjiang 212003China 

出 版 物：《Science China Chemistry》 (中国科学（化学英文版）)

年 卷 期：2020年第63卷第8期

页      面：1091-1099页

核心收录：

学科分类：081704[工学-应用化学] 081705[工学-工业催化] 07[理学] 08[工学] 0817[工学-化学工程与技术] 070303[理学-有机化学] 0703[理学-化学] 

基　　金：supported by the National Natural Science Foundation of China(21971165,21921002,81630101) the National Key Research and Development Program of China(2018YFA0903500) the“1000-Youth Talents Program”(YJ201702) the Fundamental Research Funds for the Central Universities 

主　　题：bifunctional phosphonium salts benzofused tropanes cyclic azomethine ylides cyclodearomatization antitumor activity 

摘      要：Structurally fused heterocycles encompassing a centerpiece of benzotropane are significant scaffolds with a plethora of promising biological activities,but such molecular architectures pose a long-standing daunting synthetic ***,we reported a highly efficient asymmetric cyclodearomatization of 2-nitrobenzofurans with cyclic azomethine ylides by employing bifunctional phosphonium salts as phase-transfer *** optimized reaction conditions,a diverse array of polycyclic benzofused tropane derivatives with four contiguous 4°/3°stereocenters were readily synthesized in both high yields and diastereoselectivities with up to99%*** practicality and utility of this protocol were further demonstrated by the scaled-up reaction and facile ***,preliminary investigations into their antitumor activities were also presented.