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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