Studies involving potassium permanganate mediated oxidative cyclisations of 1, 5-dienes and 1, 5, 9-trienes.
Studies involving potassium permanganate mediated oxidative cyclisations of 1, 5-dienes and 1, 5, 9-trienes.
The use of potassium permanganate to oxidatively cyclise 1,5-dienes has been well documented, albeit with disappointing yields. The aim of this study has been to optimise the reaction conditions for the oxidative cyclisation of a commercially available 1,5-diene using potassium permanganate. The optimised methodology has then been applied to a selection of readily accessible isomeric 1,5,9-trienes in order to give tetrahydrofuran lactol products with differing stereochemistry. The subsequent cleavage of the lactol products to lactones has been achieved producing four diastereoisomeric cz6'-2,5-disubstituted tetrahydrofurans in order to access potential precursors to natural molecules. biologically active and unnatural
University of Southampton
Hughes, Robert M
2462d768-a032-4abf-9c40-60d7d4fa9c12
2000
Hughes, Robert M
2462d768-a032-4abf-9c40-60d7d4fa9c12
Hughes, Robert M
(2000)
Studies involving potassium permanganate mediated oxidative cyclisations of 1, 5-dienes and 1, 5, 9-trienes.
University of Southampton, Doctoral Thesis.
Record type:
Thesis
(Doctoral)
Abstract
The use of potassium permanganate to oxidatively cyclise 1,5-dienes has been well documented, albeit with disappointing yields. The aim of this study has been to optimise the reaction conditions for the oxidative cyclisation of a commercially available 1,5-diene using potassium permanganate. The optimised methodology has then been applied to a selection of readily accessible isomeric 1,5,9-trienes in order to give tetrahydrofuran lactol products with differing stereochemistry. The subsequent cleavage of the lactol products to lactones has been achieved producing four diastereoisomeric cz6'-2,5-disubstituted tetrahydrofurans in order to access potential precursors to natural molecules. biologically active and unnatural
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Published date: 2000
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Local EPrints ID: 464413
URI: http://eprints.soton.ac.uk/id/eprint/464413
PURE UUID: db76ff79-bff3-48b2-af01-9da8d90e430e
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Date deposited: 04 Jul 2022 23:35
Last modified: 16 Mar 2024 19:29
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Author:
Robert M Hughes
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