Dedicated to the 60th Anniversary of Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences.
Enantioselective Synthesis of the Diazatricyclic Core of Alkaloid TAN1251C via an Iodoaminocyclization Reaction†
Article first published online: 30 SEP 2010
Copyright © 2010 SIOC, CAS, Shanghai & WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Chinese Journal of Chemistry
Special Issue: 60th Anniversary of Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences
Volume 28, Issue 9, pages 1717–1724, September, 2010
How to Cite
Zhang, H., Lin, Z., Huang, H., Huo, H., Huang, Y., Ye, J. and Huang, P. (2010), Enantioselective Synthesis of the Diazatricyclic Core of Alkaloid TAN1251C via an Iodoaminocyclization Reaction. Chin. J. Chem., 28: 1717–1724. doi: 10.1002/cjoc.201090290
- Issue published online: 30 SEP 2010
- Article first published online: 30 SEP 2010
- Manuscript Accepted: 13 AUG 2010
- Manuscript Received: 22 JUL 2010
- the National Natural Science Foundation of China. Grant Number: 20672089
- asymmetric synthesis
A concise enantioselective synthesis of the diazatricyclic core of alkaloid TAN1251C is reported. The method featured a stereoselective formation of the iodide intermediate 16b (in 2:1 ratio) from homoallylic amine 11b by iodine-promoted iodoaminocyclization, a previously claimed to be unsuccessful reaction. The intermediate 16b was converted to the tricyclic core of TAN1251C 28 in five steps. During this study, two unexpected products 22 and 25 were obtained, and compound 23, derived from 11a was shown to be unsuitable for the oxidative formation of the enamide of TAN1251C.