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

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JournalTetrahedron
DatePublished - 10 Sep 2007
Issue number37
Volume63
Number of pages5
Pages (from-to)9124-9128
Original languageEnglish

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.

Bibliographical note

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.

    Research areas

  • 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

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