Asymmetric Total Syntheses of Kopsane Alkaloids via a PtCl<sub>2</sub>‐Catalyzed Intramolecular [3+2] Cycloaddition
Xuelei Jia, Honghui Lei, Feipeng Han, Tao Zhang, Ying Chen, Zhengshuang Xu, Pratanphorn Nakliang, Sun Choi, Yian Guo, Tao Ye
Abstract
Abstract A concise and asymmetric total synthesis of five kopsane alkaloids that share a unique heptacyclic caged ring system was accomplished. The key transformation in the sequence involved a remarkable PtCl 2 ‐catalyzed intramolecular [3+2] cycloaddition, which allowed for the rapid assembly of pentacyclic carbon skeletons bearing 2,3‐quaternary functionalized indoline. Expeditious construction of diverse indoline scaffolds with excellent control of diastereoselectivity demonstrated the broad scope and versatility of this key transformation.
Topics & Concepts
Intramolecular forceCycloadditionIndolineChemistryRing (chemistry)StereochemistryCatalysisTotal synthesisCombinatorial chemistryEnantioselective synthesisOrganic chemistryAlkaloids: synthesis and pharmacologyChemical synthesis and alkaloidsMarine Sponges and Natural Products