| Summary: | <p>This thesis describes the development of synthetic strategies towards the densely functionalised pyrrolidinone core of the polyene β-lactone-γ-lactam antibiotic oxazolomycin A.</p> <p><strong>Chapter 1 The oxazolomycins</strong></p> <p>The oxazolomycins, a unique class of biologically active molecules containing a spiro-fused β-lactone-γ-lactam ring system are introduced. The isolation, structural elucidation and biological properties of the oxazolomycins as well as those of the structurally related inthomycins are reviewed.</p> <p><strong>Chapter 2 Previous syntheses</strong></p> <p>The two total syntheses of neooxazolomycin and the synthetic approaches to the pyrrolidinone core of oxazolomycin A and KSM-2690 B are evaluated.</p> <p><strong>Chapter 3 Project aims</strong></p> <p>An outline of the synthetic strategy employed in this project and details of the novel retrosynthesis of the pyrrolidinone core of oxazolomycin A are discussed.</p> <p><strong>Chapter 4 Synthetic studies towards the pyrrolidinone core of oxazolomycin A</strong></p> <p>The synthetic studies carried out towards the pyrrolidinone core of oxazolomycin A are described in detail. The preparation of an advanced intermediate containing the five chiral centres, four of which are contiguous, was achieved in twenty steps as a single diastereomer and as a single enantiomer.</p> <p><strong>Chapter 5 Synthetic studies towards the middle fragment of oxazolomycin A</strong></p> <p>A novel synthetic approach to the diene fragment contained in oxazolomycin A is reported. The formal synthesis of a dienyl iodide, in four fewer steps than previously reported was accomplished.</p> <p><strong>Chapter 6 Conclusions and future work</strong></p> <p>A summary of the synthetic work reported in this thesis and proposals for future study are presented.</p> <p><strong>Chapter 7 Experimental</strong></p> <p>Full experimental procedures and characterisation of compounds are reported.</p> <p><strong>Chapter 8 References</strong></p> <p>A complete list of citations employed in the previous seven chapters is provided.</p>
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