Quick assembly of 1-alkylidenyl-tetrahydroisoquinolines via a Catellani reaction/NBS-mediated cyclization sequence and synthetic applications  

作　　者：Shihu Jia Miao Bai Siwei Zhou Ruiqing Sheng Hong-Gang Cheng Qianghui Zhou 

机构地区：[1]Sauvage Center for Molecular Sciences,Engineering Research Center of Organosilicon Compounds&Materials(Ministry of Education),Hubei Key Lab on Organic and Polymeric OptoElectronic Materials,College of Chemistry and Molecular Sciences,Wuhan University,Wuhan 430072,China [2]The Institute for Advanced Studies,Wuhan University,Wuhan 430072,China [3]TaiKang Center for Life and Medical Sciences,Wuhan University,Wuhan 430072,China

出　　处：《Science China Chemistry》2023年第11期3136-3140,共5页中国科学（化学英文版）

基　　金：supported by the National Natural Science Foundation of China(21801193,21871213 and 22071189);the Natural Science Foundation of Jiangsu Province(BK20210119,Hong-Gang Cheng);the Fundamental Research Funds for the Central Universities(2042021kf0214 and 2042020kf0039);the Start-up Funding from Wuhan University。

摘　　要：We herein disclose a modular synthesis of 1-bromomethylene-THIQs involving a Catellani reaction of aryl iodides,aziridines,and terminal alkynes followed by an N-bromosuccinimide(NBS)-mediated cyclization.This approach features mild reaction conditions,wide substrate scope,good step-economy and good scalability.Based on this new method,we have accomplished the concise total synthesis of(±)-cularine,formal synthesis of 8-oxopseudopalmatine as well as the first total synthesis of dactyllactone A,demonstrating the wide synthetic potential of this method.

关 键 词：1-bromomethylene-THIQ Catellani reaction (±)-cularine 8-oxopseudopalmatine dactyllactone A 

分 类 号：O626[理学—有机化学]