Cascade metathesis reactions for the synthesis of taxane and isotaxane derivatives

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
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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Project CodeAward NoProject NamePrincipal InvestigatorFunder's NameFunder RefLead Dept
419371Quota doctoral training account (DTA)Graeme CookeBiotechnology and Biological Sciences Research Council (BBSRC)BB/D526310/1CHEM - CHEMISTRY