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 

机构地区：[1]Key Laboratory of Green Chemistry&Technology,Ministry of Education,College of Chemistry,Sichuan University,Chengdu 610064,China [2]National Chengdu Center for Safety Evaluation of Drugs and National Clinical Research Center for Geriatrics,West China Hospital,Sichuan University,Chengdu 610064,China [3]School of Environmental and Chemical Engineering,Jiangsu University of Science and Technology,Zhenjiang 212003,China

出　　处：《Science China Chemistry》2020年第8期1091-1099,共9页中国科学（化学英文版）

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。

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 challenge.Herein,we reported a highly efficient asymmetric cyclodearomatization of 2-nitrobenzofurans with cyclic azomethine ylides by employing bifunctional phosphonium salts as phase-transfer catalysts.Under 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 to>99%ee.The practicality and utility of this protocol were further demonstrated by the scaled-up reaction and facile elaborations.Moreover,preliminary investigations into their antitumor activities were also presented.

关 键 词：bifunctional phosphonium salts benzofused tropanes cyclic azomethine ylides cyclodearomatization antitumor activity 

分 类 号：O643.36[理学—物理化学] O626[理学—化学]