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

16 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

Bibliographical note

Funding Information:
We acknowledge financial support from the National Natural Science Foundation of China (21772009, 21901013), the Shenzhen Peacock Plan (KQTD2015071714043444), the Shenzhen Science and Technology Innovation Commission (JCYJ20170818090017617, JCYJ20170818090238288), the GDNSF (2014B030301003), the National Research Foundation of Korea (NRF) grants funded by the Ministry of Science and ICT (MSIT; NRF-2017R1A2B4010084, 2018R1A5A2025286, NRF-2019M3E5D4065251), and a Peng Cheng Scholar (to S.C.). Moreover, we thank the Korea Institute of Science and Technology Information (KISTI) Supercomputing Center for providing computing resources. This work was also inspired by the international and interdisciplinary environments of the JSPS Asian CORE Program, “Asian Chemical Biology Initiative”.

Funding Information:
We acknowledge financial support from the National Natural Science Foundation of China (21772009, 21901013), the Shenzhen Peacock Plan (KQTD2015071714043444), the Shenzhen Science and Technology Innovation Commission (JCYJ20170818090017617, JCYJ20170818090238288), the GDNSF (2014B030301003), the National Research Foundation of Korea (NRF) grants funded by the Ministry of Science and ICT (MSIT; NRF‐2017R1A2B4010084, 2018R1A5A2025286, NRF‐2019M3E5D4065251), and a Peng Cheng Scholar (to S.C.). Moreover, we thank the Korea Institute of Science and Technology Information (KISTI) Supercomputing Center for providing computing resources. This work was also inspired by the international and interdisciplinary environments of the JSPS Asian CORE Program, “Asian Chemical Biology Initiative”.

Publisher Copyright:
© 2020 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim

Keywords

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

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