Towards the enantioselective synthesis of Plakortide P and its application to the development of drugs for the treatment of Chagas disease
dc.check.date | 2020-08-16T11:45:53Z | |
dc.check.embargoformat | E-thesis on CORA only | en |
dc.check.entireThesis | Entire Thesis Restricted | |
dc.check.info | Restricted to everyone for five years | en |
dc.check.opt-out | Not applicable | en |
dc.check.reason | This thesis is due for publication or the author is actively seeking to publish this material | en |
dc.contributor.advisor | O'Sullivan, Timothy P. | en |
dc.contributor.author | O'Reilly, Kate | |
dc.contributor.funder | Irish Research Council for Science Engineering and Technology | en |
dc.date.accessioned | 2015-08-18T11:45:53Z | |
dc.date.issued | 2014 | |
dc.date.submitted | 2014 | |
dc.description.abstract | The 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.sponsorship | Irish Research Council for Science Engineering and Technology (IRCSET R13368) | en |
dc.description.status | Not peer reviewed | en |
dc.description.version | Accepted Version | |
dc.format.mimetype | application/pdf | en |
dc.identifier.citation | O'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.endpage | 306 | |
dc.identifier.uri | https://hdl.handle.net/10468/1920 | |
dc.language.iso | en | en |
dc.publisher | University College Cork | en |
dc.rights | © 2014, Kate O'Reilly. | en |
dc.rights.uri | http://creativecommons.org/licenses/by-nc-nd/3.0/ | en |
dc.subject | Chagas disease | en |
dc.subject | Plakortide P | en |
dc.subject | Peroxidation | en |
dc.subject | Asymmetric synthesis | en |
dc.thesis.opt-out | false | |
dc.title | Towards the enantioselective synthesis of Plakortide P and its application to the development of drugs for the treatment of Chagas disease | en |
dc.type | Doctoral thesis | en |
dc.type.qualificationlevel | Doctoral | en |
dc.type.qualificationname | PhD (Science) | en |
ucc.workflow.supervisor | tim.osullivan@ucc.ie |
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