Asymmetric Synthesis of Bioactive Lactones and the Development of a Catalytic Asymmetric Synthesis of α-Aryl Ketones

1. Front Matter

   Pages i-xxi

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2. Introduction to the Total Synthesis of Lactone-Containing Natural Products Using ZrCl4

   • Robert Doran

   Pages 1-11

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3. Asymmetric Synthesis of the β-Methyl-Substituted Analogues of (+)-Tanikolide and (–)-Malyngolide

   • Robert Doran

   Pages 13-34

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4. Asymmetric Synthesis of Both Enantiomers of a δ-Lactone Analogue of Muricatacin

   • Robert Doran

   Pages 35-56

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5. Introduction to the Development of a Catalytic Asymmetric Synthesis of Tertiary α-Aryl Ketones

   • Robert Doran

   Pages 57-102

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6. A Stereoselective Switch: Enantiodivergent Approach to the Synthesis of Isoflavanones

   • Robert Doran

   Pages 103-125

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7. Asymmetric Synthesis of Tertiary α-Aryl Ketones by Decarboxylative Asymmetric Protonation

   • Robert Doran

   Pages 127-175

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8. Back Matter

   Pages 177-202

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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.

• Antimicrobial Activity
• Asymmetric Synthesis
• Catalytic Asymmetric Synthesis
• Dual Stereocontrol
• Natural Product Analogues
• Total Synthesis

• Department of Chemistry, Imperial College London, London, United Kingdom

  Robert Doran

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.

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