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

被引：10
作者：
Xie, Shengling [1 ,2 ,3 ,4 ]
Ning, Chengqing [1 ,2 ,3 ,4 ]
Yu, Qingzhen [1 ,2 ,3 ,4 ]
Hou, Jieping [1 ,2 ,3 ,4 ]
Xu, Jing [1 ,2 ,3 ,4 ]
机构：
[1] Southern Univ Sci & Technol, Dept Chem, Shenzhen 518055, Guangdong, Peoples R China
[2] Southern Univ Sci & Technol, Shenzhen Grubbs Inst, Shenzhen 518055, Guangdong, Peoples R China
[3] Southern Univ Sci & Technol, Guangdong Prov Key Lab Catalysis, Shenzhen 518055, Guangdong, Peoples R China
[4] Southern Univ Sci & Technol, Shenzhen Key Lab Small Mol Drug Discovery & Synth, Shenzhen 518055, Guangdong, Peoples R China
来源：
CHINESE JOURNAL OF CHEMISTRY | 2021年 / 39卷 / 01期
基金：
中国国家自然科学基金;
关键词：
Protecting‐ group‐ free; Total synthesis; Spirooxindole; Alkaloid; Asymmetric synthesis; ASYMMETRIC TOTAL-SYNTHESIS; ORGANOCATALYZED CASCADE REACTIONS; ENANTIOSELECTIVE TOTAL-SYNTHESIS; BIOMIMETIC TOTAL-SYNTHESIS; PICTET-SPENGLER; SPIROTRYPROSTATIN-B; STEREOSELECTIVE-SYNTHESIS; MICHAEL ADDITION; NATURAL-PRODUCTS; UNIFIED APPROACH;
D O I：
10.1002/cjoc.202000460
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
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.
引用
收藏
页码：137 / 142
页数：6
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