Clarke, Paul A., Rolla, Gabriele A., Cridland, Andrew P. and Gill, Andrew A. (2007) An improved synthesis of (2E,4Z)-6-(benzyloxy)-4-bromohexa-2,4-dien-1-ol. Tetrahedron. pp. 9124-9128. ISSN 0040-4020
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Abstract
An improved synthesis of (2E,4Z)-6-(benzyloxy)-4-bromohexa-2,4-dien-1-ol has been devised. This new route increases the throughput and yield of the diene product by circumventing a low yielding preparation of boronic acid intermediate as well as removing the need to use multi-gram quantities of highly toxic thallium salts. In the process of developing this new route, a higher yielding preparation of ( E)-3-hydroxyprop-1-enylboronic acid was also achieved. (c) 2007 Elsevier Ltd. All rights reserved.
| Item Type: | Article |
|---|---|
| Copyright, Publisher and Additional Information: | Copyright © 2007 Elsevier B.V.. This is an author produced version of a paper subsequently published in Tetrahedron. Uploaded in accordance with the publisher's self-archiving policy. |
| Keywords: | functionalised dienes, hexacyclinic acid, (E)-3-hydroxyprop-1-enylboronic acid, scaleable synthesis, DIELS-ALDER REACTION, ENANTIOSELECTIVE SYNTHESIS, ASYMMETRIC-SYNTHESIS, HEXACYCLINIC ACID, BOTTOM-HALF, FR182877, RING, CHLOROTHRICOLIDE, SYSTEM |
| Academic Units: | The University of York > Chemistry (York) |
| Depositing User: | Ms Diana Hilmer |
| Date Deposited: | 12 Oct 2007 17:34 |
| Last Modified: | 19 Feb 2013 11:33 |
| Published Version: | http://dx.doi.org/10.1016/j.tet.2007.06.071 |
| Status: | Published |
| Refereed: | Yes |
| Related URLs: | |
| URI: | http://eprints.whiterose.ac.uk/id/eprint/3374 |
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