Ma, C., Letort, A., Aouzal, R., Wilkes, A., Maiti, G., Farrugia, L. J., Ricard, L. and Prunet, J. (2016) Cascade metathesis reactions for the synthesis of taxane and isotaxane derivatives. Chemistry: A European Journal, 22(20), pp. 6891-6899. (doi: 10.1002/chem.201600592) (PMID:27062670) (PMCID:PMC4982030)
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Abstract
Tricyclic isotaxane and taxane derivatives and have been synthesized by a very efficient cascade ring-closing dienyne metathesis (RCDEYM) reaction, which formed the A and B rings in one operation. When the alkyne is present at C13 (with no neighboring gem-dimethyl group), the RCEDYM reaction leads to 14,15-isotaxanes 16a,b and 18b with the gem-dimethyl group on the A ring. If the alkyne is at the C11 position (and thus flanked by a gem-dimethyl group), RCEDYM reaction only proceeds in the presence of a trisubstituted olefin at C13, which disfavors the competing diene ring-closing metathesis reaction, to give the tricyclic core of Taxol 44.
Item Type: | Articles |
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Additional Information: | Financial support for this work was provided by the CNRS, the Ecole Polytechnique, the University of Glasgow and the BBSRC (doctoral fellowship for A.W. BB/D526310/1). We thank Dr. Brian Millward for a generous donation. |
Status: | Published |
Refereed: | Yes |
Glasgow Author(s) Enlighten ID: | Farrugia, Dr Louis and Prunet, Dr Joelle |
Authors: | Ma, C., Letort, A., Aouzal, R., Wilkes, A., Maiti, G., Farrugia, L. J., Ricard, L., and Prunet, J. |
College/School: | College of Science and Engineering > School of Chemistry |
Journal Name: | Chemistry: A European Journal |
Publisher: | Wiley-VCH Verlag GmbH & Co. KGaA |
ISSN: | 0947-6539 |
ISSN (Online): | 1521-3765 |
Published Online: | 08 April 2016 |
Copyright Holders: | Copyright © 2016 The Authors |
First Published: | First published in Chemistry: A European Journal 22(20):6891-6899 |
Publisher Policy: | Reproduced under a Creative Commons License |
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