We thank Professor Emeritus Shin-ichiro Sakai and Professor Hiromitsu Takayama of Chiba University for providing a sample of natural nominine.
Total Synthesis of (±)-Nominine, a Heptacyclic Hetisine-Type Aconite Alkaloid†
Article first published online: 1 SEP 2004
Copyright © 2004 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Angewandte Chemie International Edition
Volume 43, Issue 35, pages 4646–4649, September 6, 2004
How to Cite
Muratake, H. and Natsume, M. (2004), Total Synthesis of (±)-Nominine, a Heptacyclic Hetisine-Type Aconite Alkaloid. Angew. Chem. Int. Ed., 43: 4646–4649. doi: 10.1002/anie.200460332
- Issue published online: 1 SEP 2004
- Article first published online: 1 SEP 2004
- Manuscript Received: 15 APR 2004
- radical reactions;
- natural products;
- total synthesis
The barrier has finally been lifted to the synthesis of hetisine-type alkaloids with the total synthesis of (±)-nominine (1) in 40 steps from 2-bromo-5-methoxyphenethyl iodide. Key steps in the construction of the architecturally complex polycyclic structure of this natural product were a radical cyclization of an enyne and a palladium-catalyzed intramolecular α arylation of an aldehyde.