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- Title
Total Syntheses of Kopsaporine, Kopsinol and Kopsiloscine A.
- Authors
Tian, Hongchang; Wu, Yinxia; Li, Xiujuan; Hao, Zhen; He, Wenyan; Huang, Xiangdi; Chen, Wen; Zhang, Hongbin
- Abstract
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.
- Subjects
NATURAL products; RADICALS (Chemistry); ALKENES; IRIDIUM; MOIETIES (Chemistry)
- Publication
Angewandte Chemie, 2023, Vol 135, Issue 15, p1
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.202218935