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Cyclisation of 1,2-dioxines containing tethered hydroxyl and carboxylic acid functionality: synthesis of tetrahydrofurans and dihydrofuran-2(3H)-ones |
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| Authors: | Ondrej Zvarec Dennis K. Taylor Edward R.T. Tiekink |
| Affiliation: | a Discipline of Wine and Horticulture, The University of Adelaide, South Australia 5005, Australia b Discipline of Chemistry, The University of Adelaide, South Australia 5005, Australia c Department of Chemistry, University of Malaya, Kuala Lumpur 50603, Malaysia |
| 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. |
| Keywords: | 1,2-Dioxine Tetrahydrofurans Dihydrofuran-2(3H)-ones Cyclisation |
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