We thank Dr. Vijay Kumar for his assistance in providing starting materials. We also thank NSERCC (Ottawa) for financial support.
Total Synthesis of Ouabagenin and Ouabain†
Article first published online: 8 JAN 2008
Copyright © 2008 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Angewandte Chemie International Edition
Volume 47, Issue 7, pages 1272–1275, February 1, 2008
How to Cite
Zhang, H., Sridhar Reddy, M., Phoenix, S. and Deslongchamps, P. (2008), Total Synthesis of Ouabagenin and Ouabain. Angew. Chem. Int. Ed., 47: 1272–1275. doi: 10.1002/anie.200704959
- Issue published online: 25 JAN 2008
- Article first published online: 8 JAN 2008
- Manuscript Received: 26 OCT 2007
- NSERCC (Ottawa)
- cardioactive agents;
- total synthesis
The highly oxygenated steroid ouabagenin (1 b) and its glycoside ouabain (1 a) were prepared by a strategy based on a polyanionic cyclization. Starting building blocks A and B were combined to give the key intermediate C and transformed into 1 b in 27 steps. Finally, ouabagenin (1 b) was converted into ouabain (1 a) in six steps (see scheme).