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Type: Journal article
Title: Cyclisation of 1,2-dioxines containing tethered hydroxyl and carboxylic acid functionality: synthesis of tetrahydrofurans and dihydrofuran-2(3H)-ones
Author: Zvarec, O.
Avery, T.
Taylor, D.
Tiekink, E.
Citation: Tetrahedron: the international journal for the rapid publication of full original research papers and critical reviews in organic chemistr, 2010; 66(4):1007-1013
Publisher: Pergamon-Elsevier Science Ltd
Issue Date: 2010
ISSN: 0040-4020
Statement of
Ondrej Zvarec, Thomas D. Avery, Dennis K. Taylor and Edward R.T. Tiekink
Abstract: Herein we outline cyclisations of tethered hydroxyl and carboxylic acid moieties onto the olefinic motif of 1,2-dioxines to generate tetrahydrofurans and dihydrofuran-2(3H)-ones, whilst maintaining the peroxide linkage intact. This work demonstrates the first examples of intramolecular cyclisation of tethered hydroxyl groupings onto 1,2-dioxines generating functionalised THFs in a highly stereoselective manner and includes improved methods for previously reported carboxylic acid tether cyclisations. Additionally, improved methods for the oxidation of 1,2-dioxines containing tethered alcohols to furnish tethered carboxylic acids are also detailed. Subsequent reduction of the peroxide linkage enables the generation of functionalised tetrahydrofurans and dihydrofuran-2(3H)-ones, which are useful building blocks for the construction of natural products. © 2009 Elsevier Ltd. All rights reserved.
Keywords: 1,2-Dioxine
Rights: (c) 2009 Elsevier Ltd. All rights reserved
DOI: 10.1016/j.tet.2009.11.068
Grant ID: ARC
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