Synthetic Studies on Natural Products, 53; Part 52: D. B. Shinde, B. S. Kanth, M. Srilatha, B. Das, Synthesis2011, in press.
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Full Paper
The First Stereoselective Total Synthesis of Putaminoxin E and Its Epimer and Evaluation of Their Biological Properties†
Article first published online: 9 DEC 2011
DOI: 10.1002/ejoc.201101601
Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
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How to Cite
Sudhakar, C., Reddy, P. R., Kumar, C. G., Sujitha, P. and Das, B. (2012), The First Stereoselective Total Synthesis of Putaminoxin E and Its Epimer and Evaluation of Their Biological Properties. Eur. J. Org. Chem., 2012: 1253–1258. doi: 10.1002/ejoc.201101601
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Publication History
- Issue published online: 13 FEB 2012
- Article first published online: 9 DEC 2011
- Manuscript Received: 4 NOV 2011
Funded by
- Council of Scientific and Industrial Research
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Keywords:
- Natural products;
- Kinetic resolution;
- Metathesis;
- Enantioselectivity;
- Biological activity
Abstract
Putaminoxin E, a natural nonanolide, and its C-9 epimer were synthesized for the first time starting from pentane-1,5-diol and butyraldehyde. The synthetic sequences involve Maruoka asymmetric allylation, Sharpless kinetic resolution, and ring-closing metathesis as the key steps. The cytotoxic and antimicrobial activities of these compounds were evaluated.