- Title
- Cascade metathesis reactions for the synthesis of taxane and isotaxane derivatives
- Creator
- Ma, Cong; Letort, Aurélien; Aouzal, Rémi; Wilkes, Antonia; Maiti, Gourhari; Farrugia, Louis J.; Ricard, Louis; Prunet, Joëlle
- Relation
- Chemistry - A European Journal Vol. 22, Issue 20, p. 6891-6898
- Publisher Link
- http://dx.doi.org/10.1002/chem.201600592
- Publisher
- Wiley- V C H Verlag GmbH & Co. KGaA
- Resource Type
- journal article
- Date
- 2016
- Description
- Tricyclic isotaxane and taxane derivatives 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 16 a,b and 18 b 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.
- Subject
- synthesis; cascade metathesis reactions; taxane; isotaxane; derivatives
- Identifier
- http://hdl.handle.net/1959.13/1346532
- Identifier
- uon:29882
- Identifier
- ISSN:0947-6539
- Rights
- Copyright 2016 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the Creative Commons Attribution License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.
- Language
- eng
- Full Text
- Reviewed
- Hits: 6169
- Visitors: 6361
- Downloads: 261
| Thumbnail | File | Description | Size | Format | |||
|---|---|---|---|---|---|---|---|
| View Details Download | ATTACHMENT02 | Publisher version (open access) | 1 MB | Adobe Acrobat PDF | View Details Download |