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Title: The total synthesis of bengazole A
Author: Bull, J. A.
Awarding Body: University of Cambridge
Current Institution: University of Cambridge
Date of Award: 2007
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Bengazole A 1 is a bisoxazole marine natural product that displays potent antifungal activity. This thesis documents a total synthesis of bengazole A, the first to provide a single stereoisomer of the natural product. Section 1 contains an introduction to oxazole containing natural products and the isolation, structure determination and biological activity of the bengazoles. It goes on to review the main methods to synthesise oxazole rings and their proposed biosynthesis section 2 then examines published synthetic efforts towards the bengazoles and previous work in the Ley group towards the synthesis of bengazole A. Sections 3 to 6 comprise the results and discussion. Section 3 describes the synthesis of a carboxylic acid fragment containing the 5-substituted oxazole ring. Section 4 details a number of approaches towards the formation of the central oxazole ring of bengazole A and the successful synthesis of a bisoxazole-oxime fragment as a single enantiomer. Section 5 describes the coupling of the bisoxazole fragment and a BDA-alkene fragment by a diastereoselective 1,3-dipolar cycloaddition. This is followed by the completion of the total synthesis of bengazole A 1. The synthesis of analogues including 10-epi-bengazole A 2 and bengazole B 3 is detailed in Section 6. Section 7 provides a detailed account of experimental procedures.
Supervisor: Not available Sponsor: Not available
Qualification Name: Thesis (Ph.D.) Qualification Level: Doctoral
EThOS ID:  DOI: Not available