Asymmetric Total Syntheses of Kopsane Alkaloids via a PtCl2-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

Research output: Contribution to journalArticlepeer-review

11 Scopus citations

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 PtCl2-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.

Original languageEnglish
Pages (from-to)12832-12836
Number of pages5
JournalAngewandte Chemie - International Edition
Volume59
Issue number31
DOIs
StatePublished - 27 Jul 2020

Keywords

  • Pt catalysis
  • [3+2] cycloaddition reactions
  • alkaloids
  • kopsanes
  • natural products

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