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Please use this identifier to cite or link to this item: https://dspace.lboro.ac.uk/2134/16261

Title: Benzisoxazoles: new routes to coleophomone analogues
Authors: Chatterley, Alexander
Keywords: Chemistry
Organic
Heterocyclic
Medicinal
Lilly
Coleophomone
Isoxazole
Oxazole
Issue Date: 2014
Publisher: © Alexander Chatterley
Abstract: 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.
Description: A Doctoral Thesis. Submitted in partial fulfilment of the requirements for the award of Doctor of Philosophy of Loughborough University.
Sponsor: Loughborough University and Lilly UK
URI: https://dspace.lboro.ac.uk/2134/16261
Appears in Collections:PhD Theses (Chemistry)

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