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Title: Benzisoxazoles : new routes to coleophomone analogues
Author: Chatterley, Alexander
ISNI:       0000 0004 5357 5860
Awarding Body: Loughborough University
Current Institution: Loughborough University
Date of Award: 2014
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This project has been part of an ongoing interest in metabolites with a cyclic tricarbonyl motif 1, usually enolised. Coleophomones A C have a unique architecture with the cyclic tricarbonyl motif embedded in an 11-membered ring: A & B exist in aldol equilibrium, B & C are geometric isomers, and D lacks the macrocycle.1,2 Antifungal & antibiotic activity, and inhibition of human heart chymase & bacterial cell-wall transglycosylase, has generated synthetic interest. In an approach distinct from reported studies,3 we propose 4-carbonyl-substituted isoxazoles, from dipolar cycloaddition of nitrile oxides, as building blocks for the tricarbonyl framework. During this investigation precursors to the macrocycles of coleophomones A, B, C and analogues were developed. En route to these precursors we have uncovered and probed a facile and highly unusual benzisoxazole to oxazole rearrangement. *Schemes and figures relating to the abstract can be found within the document proper.
Supervisor: Not available Sponsor: Loughborough University ; Lilly UK
Qualification Name: Thesis (Ph.D.) Qualification Level: Doctoral
EThOS ID:  DOI: Not available
Keywords: Chemistry ; Organic ; Heterocyclic ; Medicinal ; Lilly ; Coleophomone ; Isoxazole ; Oxazole