期刊
CHEMISTRY-A EUROPEAN JOURNAL
卷 19, 期 13, 页码 4255-4261出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201203454
关键词
cage compounds; C-C coupling; heterocyclic compounds; natural products; polycyclic compounds; synthetic methods
资金
- Ministry of Education, Culture, Sports, Science, and Technology, Japan [19790019, 20249006]
- Grants-in-Aid for Scientific Research [25460019, 24590142, 23659058, 20249006, 19790019] Funding Source: KAKEN
Scholarisine A, isolated from the leaves of Alstonia scholaris, is a monoterpene indole alkaloid with an unprecedented cage-like structure. In this paper, preparation of the distinctive cage-like core skeleton of scholarisine A is described. The key feature of this synthetic strategy is an intramolecular oxidative coupling reaction at the late stage to construct a 10-oxa-tricyclo[5.3.1.0(3,8)]undecan-9-one structure fused with indolenine. Intramolecular oxidative coupling by using N-iodosuccinimide gave the carbon framework of scholarisine A in moderate yield, which is the first example of intramolecular oxidative-coupling reaction between non-activated enolate and indole. This study lays the foundation for continued investigations towards the total synthesis of scholarisine A.
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