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An improved synthesis of (2E,4Z)-6-(benzyloxy)-4-bromohexa-2,4-dien-1-ol

Clarke, Paul A. (orcid.org/0000-0003-3952-359X), 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
Institution: The University of York
Academic Units: The University of York > Chemistry (York)
Depositing User: Ms Diana Hilmer
Date Deposited: 12 Oct 2007 17:34
Last Modified: 22 Mar 2016 00:04
Published Version: http://dx.doi.org/10.1016/j.tet.2007.06.071
Status: Published
Refereed: Yes
URI: http://eprints.whiterose.ac.uk/id/eprint/3374

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