羟醛反应
化学
全合成
部分
分子内力
烯烃纤维
亲核细胞
戒指(化学)
立体化学
烷基化
自由基环化
碳骨架
有机化学
催化作用
作者
Hong Bin Zhang,Hong-Chang Tian,Yinxia Wu,Xiujuan Li,Zhen Hao,Wenya He,Xiangdi Huang,Wen Chen
标识
DOI:10.1002/anie.202218935
摘要
Kopsia alkaloids represent a complex class of natural products bearing a polycyclic ring system with two or three consecutive quaternary carbon centers. In this article, we report the first total synthesis of Kopsaporine related alkaloids. Features of our structure-unit-based strategy are an intramolecular Pummerer rearrangement induced nucleophilic cyclization/aza-Prins cyclization to construct the highly functional hexahydrocarbazole skeleton, an olefin migration vinylogous alkylation to establish the C20 all-carbon quaternary center, an iridium complex mediated radical addition to fuse the aspidofractine framework, an unprecedented IBX oxidation to introduce the α-hydroxyketone moiety, and a bioinspired retro-Aldol/Aldol reaction to convert kopsaporine to kopsiloscine A.
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