Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 59, Issue 31, Pages 12832-12836Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.202005048
Keywords
[3+2] cycloaddition reactions; alkaloids; kopsanes; natural products; Pt catalysis
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Funding
- National Natural Science Foundation of China [21772009, 21901013]
- Shenzhen Peacock Plan [KQTD2015071714043444]
- Shenzhen Science and Technology Innovation Commission [JCYJ20170818090017617, JCYJ20170818090238288]
- GDNSF [2014B030301003]
- National Research Foundation of Korea (NRF) - Ministry of Science and ICT (MSIT) [NRF-2017R1A2B4010084, 2018R1A5A2025286, NRF-2019M3E5D4065251]
- National Research Foundation of Korea [2019M3E5D4065251] Funding Source: Korea Institute of Science & Technology Information (KISTI), National Science & Technology Information Service (NTIS)
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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.
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