Towards the enantioselective synthesis of Plakortide P and its application to the development of drugs for the treatment of Chagas disease

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dc.check.date2020-08-16T11:45:53Z
dc.check.embargoformatE-thesis on CORA onlyen
dc.check.entireThesisEntire Thesis Restricted
dc.check.infoRestricted to everyone for five yearsen
dc.check.opt-outNot applicableen
dc.check.reasonThis thesis is due for publication or the author is actively seeking to publish this materialen
dc.contributor.advisorO'Sullivan, Timothy P.en
dc.contributor.authorO'Reilly, Kate
dc.contributor.funderIrish Research Council for Science Engineering and Technologyen
dc.date.accessioned2015-08-18T11:45:53Z
dc.date.issued2014
dc.date.submitted2014
dc.description.abstractThe primary focus of this thesis was the asymmetric peroxidation of α,β-unsaturated aldehydes and the development of this methodology to include the synthesis of bioactive chiral 1,2-dioxane and 1,2-dioxalane rings. In Chapter 1 a review detailing the new and improved methods for the acyclic introduction of peroxide functionality to substrates over the last decade was discussed. These include a detailed examination of metal-mediated transformations, chiral peroxidation using organocatalytic means and the improvements in methodology of well-established peroxidation pathways. The second chapter discusses the method by which peroxidation of our various substrates was attempted and the optimisation studies associated with these reactions. The method by which the enantioselectivity of our β-peroxyaldehydes was determined is also reviewed. Chapters 3 and 4 focus on improving the enantioselectivity associated with our asymmetric peroxidation reaction. A comprehensive analysis exploring the effect of solvent, concentration and temperature on enantioselectivity was examined. The effect that different catalytic systems have on enantioselectivity and reactivity was also investigated in depth. Chapter 5 details the various transformations that β-peroxyaldehydes can undergo and the manipulation of these transformations towards the establishment of several routes for the formation of chiral 1,2-dioxane and 1,2-dioxalane rings. Chapter 6 details the full experimental procedures, including spectroscopic and analytical data for the compounds prepared during this research.en
dc.description.sponsorshipIrish Research Council for Science Engineering and Technology (IRCSET R13368)en
dc.description.statusNot peer revieweden
dc.description.versionAccepted Version
dc.format.mimetypeapplication/pdfen
dc.identifier.citationO'Reilly, K. 2014. Towards the enantioselective synthesis of Plakortide P and its application to the development of drugs for the treatment of Chagas disease. PhD Thesis, University College Cork.en
dc.identifier.endpage306
dc.identifier.urihttps://hdl.handle.net/10468/1920
dc.language.isoenen
dc.publisherUniversity College Corken
dc.rights© 2014, Kate O'Reilly.en
dc.rights.urihttp://creativecommons.org/licenses/by-nc-nd/3.0/en
dc.subjectChagas diseaseen
dc.subjectPlakortide Pen
dc.subjectPeroxidationen
dc.subjectAsymmetric synthesisen
dc.thesis.opt-outfalse
dc.titleTowards the enantioselective synthesis of Plakortide P and its application to the development of drugs for the treatment of Chagas diseaseen
dc.typeDoctoral thesisen
dc.type.qualificationlevelDoctoralen
dc.type.qualificationnamePhD (Science)en
ucc.workflow.supervisortim.osullivan@ucc.ie
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