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dc.contributor.advisorWestwood, Nicholas James
dc.contributor.authorVoûte, Nicholas
dc.coverage.spatial203en
dc.date.accessioned2008-05-15T11:03:05Z
dc.date.available2008-05-15T11:03:05Z
dc.date.issued2008
dc.identifieruk.bl.ethos.552071 
dc.identifier.urihttp://hdl.handle.net/10023/486
dc.description.abstractThis thesis describes investigations directed towards developing a novel synthetic route to the natural products perophoramidine and the communesins, with particular emphasis placed on the formation of the two vicinal all-carbon quaternary centres contained in these molecules. Chapter 1 introduces perophoramidine and the communesin group of natural products and explains how they are related to the calycanthaceous alkaloids. The isolation of perophoramidine and the communesins is outlined and their biosynthesis is discussed. Specific structural features of these natural products are highlighted before established synthetic strategies are reviewed. Chapter 1 concludes by proposing a novel synthetic route for the synthesis of perophoramidine and the communesins that involves a Claisen rearrangement in the indolo[2,3-b]quinoline system as a key step. Chapter 2 describes model studies on the proposed Claisen rearrangement in an attempt to form a quaternary centre in the indolo[2,3-b]quinoline system. These initial studies did not result in the generation of the desired quaternary centre. However, a detailed understanding of the reactions that occur leads to the design of a new model substrate. Chapter 3 describes studies on the revised model system that result in the formation of the desired quaternary centre using a Claisen rearrangement. The differences between the two systems are discussed before an investigation into the scope of the rearrangement is described. Chapter 3 concludes by describing an investigation into a protecting group strategy that would by required with this synthetic route. Chapter 4 describes investigations into the formation of the second vicinal quaternary centre using a model system. The synthetic routes investigated lead to two separate methods for the formation of the desired quaternary centre. Chapter 5 describes investigations into the effect a C-10 substituent has on the Claisen rearrangement. Additionally, an asymmetric version of the Claisen rearrangement is examined. Chapter 5 culminates in the preparation of an intermediate relevant to an asymmetric synthesis of the communesins.en
dc.format.extent2675 bytes
dc.format.mimetypeapplication/pdf
dc.language.isoenen
dc.publisherUniversity of St Andrews
dc.subjectCommunesinen
dc.subjectPerophoramidineen
dc.subjectClaisen rearrangementen
dc.subject.lccQP801.I45V7
dc.subject.lcshIndole alkaloids--Synthesisen
dc.subject.lcshClaisen rearrangementen
dc.titleRearrangements in the indolo[2,3-b]quinoline system : a novel approach to the synthesis of perophoramidine and the the communesinsen
dc.typeThesisen
dc.contributor.sponsorEngineering and Physical Sciences Research Council (EPSRC)en
dc.contributor.sponsorUniversity of St Andrews
dc.type.qualificationlevelDoctoralen
dc.type.qualificationnamePhD Doctor of Philosophyen
dc.publisher.institutionThe University of St Andrewsen
dc.rights.embargodate2018-11-19en
dc.rights.embargoreasonThesis restricted in accordance with University regulations. Electronic copy restricted until 19th November 2018en


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