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This thesis addresses two fundamental areas in contemporary organic chemistry: synthesis of natural products and catalytic asymmetric synthesis. Firstly, a new methodology, developed by our research group, which allows the asymmetric synthesis of lactones, a structural unit ubiquitous in natural products, was utilised in the synthesis of a number of natural product analogues that showed significant biological activity. Secondly, the development of a catalytic asymmetric synthesis of a key structural motif present in a number of natural products and pharmaceuticals was accomplished. During the course of this work we discovered dual stereo control, which is significant because it allows the configuration of a new stereo centre to be controlled by a simple change of proton source.
List of contents
Introduction to the Total Synthesis of Lactone-Containing Natural Products using ZrCl4.- Asymmetric Synthesis of the beta-Methyl-Substituted Analogues of (+)-Tanikolide and (-)-Malyngolide.- Asymmetric Synthesis of Both Enantiomers of a d-Lactone Analogue of Muricatacin.- Introduction to the Development of a Catalytic Asymmetric Synthesis of Tertiary -Aryl Ketones.- A Stereoselective Switch: Enantiodivergent Approach to the Synthesis of Isoflavanones.- Asymmetric Synthesis of Tertiary -Aryl Ketones by Decarboxylative Asymmetric Protonation.
About the author
Robert, from Co. Wicklow, Ireland, graduated from University College Dublin in 2010 with a 1st class Honours BSc in Chemistry completing his final year project under the supervision of Professor Pat Guiry in the synthesis of aromatic Lipoxin analogues. He was awarded an Embark Postgraduate Scholarship from the Irish Research Council (IRC) in to undertake PhD studies with Professor Pat Guiry on the total synthesis of lactone-containing natural products and catalytic asymmetric synthesis of α-aryl ketones. Following his PhD he moved to Imperial College London as a post-doctoral research associate with Dr James A. Bull working on the synthesis and functionalisation of oxetanes.
Summary
This thesis addresses two fundamental areas in contemporary organic chemistry: synthesis of natural products and catalytic asymmetric synthesis. Firstly, a new methodology, developed by our research group, which allows the asymmetric synthesis of lactones, a structural unit ubiquitous in natural products, was utilised in the synthesis of a number of natural product analogues that showed significant biological activity. Secondly, the development of a catalytic asymmetric synthesis of a key structural motif present in a number of natural products and pharmaceuticals was accomplished. During the course of this work we discovered dual stereo control, which is significant because it allows the configuration of a new stereo centre to be controlled by a simple change of proton source.
