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-fre...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.展开更多
基金Financial support from SZSTI(Nos.JCY120170817110515599,KQTD20150717103157174)the National Natural Science Founda tion of China(Nos.21772082 and 21971104)+3 种基金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.
文摘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.
