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Title: Synthesis of the pyrrolidinone core of oxazolomycin A
Author: O'Riordan, Timothy Jeremiah Cornelius
ISNI:       0000 0004 2686 4106
Awarding Body: University of Oxford
Current Institution: University of Oxford
Date of Award: 2009
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This thesis describes the development of synthetic strategies towards the densely functionalised pyrrolidinone core of the polyene β-lactone-γ-lactam antibiotic oxazolomycin A. Chapter 1 The oxazolomycins 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. Chapter 2 Previous syntheses The two total syntheses of neooxazolomycin and the synthetic approaches to the pyrrolidinone core of oxazolomycin A and KSM-2690 B are evaluated. Chapter 3 Project aims 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. Chapter 4 Synthetic studies towards the pyrrolidinone core of oxazolomycin A 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. Chapter 5 Synthetic studies towards the middle fragment of oxazolomycin A 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. Chapter 6 Conclusions and future work A summary of the synthetic work reported in this thesis and proposals for future study are presented. Chapter 7 Experimental Full experimental procedures and characterisation of compounds are reported. Chapter 8 References A complete list of citations employed in the previous seven chapters is provided.
Supervisor: Donohoe, Timothy James Sponsor: Engineering and Physical Sciences Research Council ; GlaxoSmithKline
Qualification Name: Thesis (Ph.D.) Qualification Level: Doctoral
EThOS ID:  DOI: Not available
Keywords: Organic chemistry ; Organic synthesis ; Synthetic organic chemistry ; Natural products ; Total synthesis ; Antibiotics