Protecting-Group-Free Total Synthesis and Biological Investigation of Cabucine Oxindole A  

作　　者：Shengling Xie Chengqing Ning Qingzhen Yu Jieping Hou Jing Xu 

机构地区：[1]Department of Chemistry and Shenzhen Grubbs Institute and Guangdong Provincial Key Laborotory of Catalysis and Shenzhen Key Laboratory of Small Molecule Drug Discovery and Synthesis,Southern University of Science and Technology,Shenzhen,Guangdong 518055,China

出　　处：《Chinese Journal of Chemistry》2021年第1期137-142,共6页中国化学（英文版）

基　　金：Financial support from SZSTI(Nos.JCY120170817110515599,KQTD20150717103157174);the National Natural Science Founda tion of China(Nos.21772082 and 21971104);the Guangdong Innovative Program(No.2019BT02Y335);the Guangdong Provin cial Key Laboratory of Catalysis(No.2020B121201002);the Shen zhen Key Laboratory of Small Molecule Drug Discovery and Syn thesis(No.ZDSY520190902093215877);the Shenzhen Nobel Prize Scientists Laboratory Project(C17783101)is greatly appreci-ated.The authors are grateful to Prof.Qing Ye(SUSTech)for assis-tance with XRD analysis.

摘　　要：Owing to their challenging structures and promising biological profiles,spirooxindole alkaloids have long attracted much attention from the synthetic community.Herein,we wish to describe a concise,protecting-group-free total synthesis of cabucine oxindole A,a putative natural spirooxindole alkaloid and a possible biosynthetic congener of cabucine and palmirine.Key transformations of our approach include a one-step,organocatalytic and enantioselective construction of the spiro[pyrrolidine-3,3'-oxindole]moiety and a Korte rearrangement to furnish the final dihydropyran motif.Biological investigation of 1 and its synthetic intermediates revealed lactone 2 as a mild MOLT-4 and MCF7 cell line inhibitor.

关 键 词：Protecting-group-free Total synthesis SPIROOXINDOLE ALKALOID Asymmetric synthesis 

分 类 号：O62[理学—有机化学]