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dc.contributor.authorGough, Damien Francis Christopher
dc.date.accessioned2011-07-27T09:16:10Z
dc.date.available2011-07-27T09:16:10Z
dc.date.issued2007
dc.identifier.urihttp://qmro.qmul.ac.uk/xmlui/handle/123456789/1524
dc.descriptionPhDen_US
dc.description.abstractDihydropyrans are important structural motifs that are found within many natural products and biologically active compounds. As such, a number of versatile methods have been developed for their construction. Chapter One provides several examples of interesting natural products which contain dihydropyran moieties and gives a brief summary of the existing methodology for the preparation of these heterocycles. Chapter Two gives a detailed account of the silyl-Prins reaction and explains how the methodology may be expanded to encompass new types of substituted dihydropyran. The first strategy was to develop a route to dihydropyrans with an incorporated ester moiety in the 2-position. The second strategy involved the preparation of exo-methylene tetrahydropyrans using silyl-Prins methodology. Thirdly, an investigation into the Mukaiyama-Aldol silyl-Prins reaction, as a potential route to dihydropyrans with an incorporated hydroxyethyl moiety, was performed. The first step was the development of an expedient route to a vinyl ether precursor which was then used to investigate preliminary Mukaiyama-Aldol silyl-Prins reactions. Chapter 3 provides a brief summary of the origin and pharmacology of (-)-centrolobine and kendomycin which both possess integral tetrahydropyran substructures making them attractive targets for synthesis using the silyl-Prins reaction. A literature overview of the existing methods for their syntheses is provided, with particular focus on the methodology used to construct the key tetrahydropyran core. Chapter 4 discusses the retrosynthetic analysis of (±)-centrolobine and describes the development of synthetic pathways to (±)-centrolobine which enable the silyl-Prins reaction to be employed in the key cyclisation step. Kendomycin is also retrosynthetically analysed and a number of routes to the synthesis of its integral tetrahydropyran component using the silyl-Prins methodology are investigated. Chapter 5 provides detailed experimental procedures and data for the compounds described in this thesis.en_US
dc.description.sponsorshipEngineering and Physical Science Research Council Queen Mary College
dc.language.isoenen_US
dc.subjectChemistryen_US
dc.titleNovel Routes to Substituted Dihydropyransen_US
dc.typeThesisen_US
dc.rights.holderThe copyright of this thesis rests with the author and no quotation from it or information derived from it may be published without the prior written consent of the author


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    Theses Awarded by Queen Mary University of London

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