Novel synthesis of trisubstituted olefins for the preparation of the C16–C30 fragment of dolabelide C

Tiniakos, A. F., Wittmann, S., Audic, A. and Prunet, J. (2018) Novel synthesis of trisubstituted olefins for the preparation of the C16–C30 fragment of dolabelide C. Organic Letters, 21(3), pp. 589-592. (doi:10.1021/acs.orglett.8b03552) (PMID:30589270)

Tiniakos, A. F., Wittmann, S., Audic, A. and Prunet, J. (2018) Novel synthesis of trisubstituted olefins for the preparation of the C16–C30 fragment of dolabelide C. Organic Letters, 21(3), pp. 589-592. (doi:10.1021/acs.orglett.8b03552) (PMID:30589270)

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Abstract

A silicon-tether ring-closing metathesis strategy is reported for the synthesis of trisubstituted olefins flanked by allylic or homoallylic alcohols, which are difficult to obtain by classical ring-closing or cross-metathesis reactions. In addition, a novel Peterson olefination reaction has been developed for the preparation of the allyldimethylsilane precursors, which are versatile synthetic intermediates. This method was then applied to the synthesis of the C16–C30 fragment of dolabelide C.

Item Type:Articles
Status:Published
Refereed:Yes
Glasgow Author(s) Enlighten ID:Audic, Mr Alexandre and Tiniakos, Mr Alexander and Wittmann, Mr Stephane and Prunet, Dr Joelle
Authors: Tiniakos, A. F., Wittmann, S., Audic, A., and Prunet, J.
College/School:College of Science and Engineering > School of Chemistry
Journal Name:Organic Letters
Publisher:American Chemical Society
ISSN:1523-7060
ISSN (Online):1523-7052
Copyright Holders:Copyright © 2018 American Chemical Society
First Published:First published in Organic Letters 21(3):589-592
Publisher Policy:Reproduced under a Creative Commons License

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Project CodeAward NoProject NamePrincipal InvestigatorFunder's NameFunder RefLead Dept
701101EPSRC 2015 DTPMary Beth KneafseyEngineering and Physical Sciences Research Council (EPSRC)EP/M508056/1R&I - RESEARCH STRATEGY & INNOVATION
608951Engineering and Physical Sciences Doctoral Training Grant 2012-16Mary Beth KneafseyEngineering and Physical Sciences Research Council (EPSRC)EP/K503058/1VPO VICE PRINCIPAL RESEARCH & ENTERPRISE