|dc.contributor.author||Gough, Damien Francis Christopher||
|dc.description.abstract||Dihydropyrans 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.sponsorship||Engineering and Physical Science Research Council
Queen Mary College||
|dc.title||Novel Routes to Substituted Dihydropyrans||en_US
|dc.rights.holder||The 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||