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Full Paper
Synthesis of the Carbon Framework of Scholarisine A by Intramolecular Oxidative Coupling
Article first published online: 11 FEB 2013
DOI: 10.1002/chem.201203454
Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Additional Information
How to Cite
Watanabe, T., Kato, N., Umezawa, N. and Higuchi, T. (2013), Synthesis of the Carbon Framework of Scholarisine A by Intramolecular Oxidative Coupling. Chem. Eur. J., 19: 4255–4261. doi: 10.1002/chem.201203454
Publication History
- Issue published online: 15 MAR 2013
- Article first published online: 11 FEB 2013
- Manuscript Received: 27 SEP 2012
Funded by
- Grant-in-Aid for Young Scientists (B). Grant Number: 19790019
- Grant-in-Aid for Scientific Research. Grant Number: 20249006
- Ministry of Education, Culture, Sports, Science, and Technology, Japan
Keywords:
- cage compounds;
- C
![[BOND]](http://onlinelibrarystatic.wiley.com/undisplayable_characters/00f8ff.gif)
C coupling; - heterocyclic compounds;
- natural products;
- polycyclic compounds;
- synthetic methods
Abstract
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[5.3.1.03, 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.