Cyclisation of 1,2-dioxines containing tethered hydroxyl and carboxylic acid functionality: Synthesis of tetrahydrofurans and dihydrofuran-2(3H)-ones

Zvarec, O.; Avery, T.D.; Taylor, D.K.; Tiekink, E.R.T. (2010) Cyclisation of 1,2-dioxines containing tethered hydroxyl and carboxylic acid functionality: Synthesis of tetrahydrofurans and dihydrofuran-2(3H)-ones. Tetrahedron, 66 (4). pp. 1007-1013.

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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. (C) 2009 Elsevier Ltd. All rights reserved.

Item Type: Article
Creators:
  1. Zvarec, O.
  2. Avery, T.D.
  3. Taylor, D.K.
  4. Tiekink, E.R.T.
Journal or Publication Title: Tetrahedron
Uncontrolled Keywords: 1,2-Dioxine; Tetrahydrofurans; Dihydrofuran-2(3H)-ones; Cyclisation
Subjects: Q Science > Q Science (General)
Divisions: UNSPECIFIED
Depositing User: MR Faizal II H
Date Deposited: 23 Dec 2015 11:15
Last Modified: 23 Dec 2015 11:15
URI: http://eprints.um.edu.my/id/eprint/15263

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