Dedicated to Professor Philip Kocienski, FRS
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Full Paper
An Ammonia-Triggered Stereocontrolled Conversion of a γ-Lactone to the Central Tetrahydropyran of Pederin, Psymberin, and Onnamides D–F†
Article first published online: 11 JAN 2012
DOI: 10.1002/ejoc.201101543
Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Additional Information
How to Cite
Buffham, W. J., Swain, N. A., Kostiuk, S. L., Gonçalves, T. P. and Harrowven, D. C. (2012), An Ammonia-Triggered Stereocontrolled Conversion of a γ-Lactone to the Central Tetrahydropyran of Pederin, Psymberin, and Onnamides D–F. Eur. J. Org. Chem., 2012: 1217–1222. doi: 10.1002/ejoc.201101543
- †
Publication History
- Issue published online: 13 FEB 2012
- Article first published online: 11 JAN 2012
- Manuscript Received: 21 OCT 2011
Funded by
- Pfizer
- Engineering and Physical Sciences Research Council (EPSRC)
- European Regional Development Fund (ERDF). Grant Number: Innovative Synthesis: Culture and Entrepreneurship in Chemistry (IS:CE) – Chem. & InterReg IVa program 4061
Keywords:
- Lactones;
- Oxygen heterocycles;
- Ring expansion;
- Cyclization;
- Synthesis design
Abstract
The onnamides, pederin, and psymberin have each attracted attention because of their potent biological activity and interesting structural features. A short (eight steps) and efficient stereocontrolled route to the central tetrahydropyran ring in these natural products has been developed from (S)-malic acid. The key sequence involves the conversion of a γ-lactone to a tetrahydropyran structure triggered by the addition of ammonia.