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Protecting‐Group‐Free Total Synthesis and Biological Investigation of Cabucine Oxindole A †
Author(s) -
Xie Shengling,
Ning Chengqing,
Yu Qingzhen,
Hou Jieping,
Xu Jing
Publication year - 2021
Publication title -
chinese journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 1001-604X
DOI - 10.1002/cjoc.202000460
Subject(s) - chemistry , oxindole , total synthesis , pyrrolidine , protecting group , enantioselective synthesis , stereochemistry , moiety , combinatorial chemistry , organic chemistry , catalysis , alkyl
Main observation and conclusion 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.