We would like to thank the EPSRC/Pharma Organic Synthetic Chemistry Studentships program for supporting this project and GlaxoSmithKline for financial support. We also thank Diamond Light Source for an award of beamtime on I19 (MT1858) and Dr. K. E. Christensen for support.
A Short and Efficient Synthesis of Neodysiherbaine A by Using Catalytic Oxidative Cyclization†
Article first published online: 27 JUN 2011
Copyright © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Angewandte Chemie International Edition
Volume 50, Issue 33, pages 7604–7606, August 8, 2011
How to Cite
Donohoe, T. J., Winship, P. C. M., Tatton, M. R. and Szeto, P. (2011), A Short and Efficient Synthesis of Neodysiherbaine A by Using Catalytic Oxidative Cyclization. Angew. Chem. Int. Ed., 50: 7604–7606. doi: 10.1002/anie.201102525
- Issue published online: 5 AUG 2011
- Article first published online: 27 JUN 2011
- Manuscript Received: 12 APR 2011
- natural products;
- oxidative cyclization;
- oxocarbenium ions;
- total synthesis
To the point: The synthesis of the title compound was achieved with 24 % overall yield through a sequence that has just seven linear steps (see scheme). Key points are the facial selectivity displayed by an oxocarbenium ion derived from a ribopyranose system and an osmium-catalyzed oxidative cyclization that is compatible with several acid-sensitive groups.