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Title: Studies towards the total synthesis of antascomicin A
Author: Barlow, J.
Awarding Body: University of Cambridge
Current Institution: University of Cambridge
Date of Award: 1999
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The first part describes the discovery and the biological properties of the natural product antascomicin A. The biological properties of the structurally related immunosuppressant natural products rapamycin and FK-506 are also discussed. The second section reviews methods to date of synthesising the masked tricarbonyl unit which is present in antascomicin A, rapamycin, and FK-506. This includes both literature material and the novel Ley group strategies. Part three outlines the retrosynthetic analysis of antascomicin A that has been developed by the Ley group. Section four details the research that has been completed to date. The routes to the C10-C16 aldehyde and the C17-C24 vinyl iodide are described. This includes an account of the extensive investigations into the formation of the C21-C22 trans double bond. Two successful approaches to the key coupling of the C10-C16 aldehyde with the C17 -C24 vinyl iodide to form the C10-C24 allylic alcohol are detailed, and the subsequent synthesis of the protected C10-C24 fragment is described. Investigations into the synthesis of the C25-C34 fragment are also presented. The coupling of a model stannane with the novel C30-C33 tartrate derived, butane2, 3-diacetal protected aldehyde under various Lewis acid conditions is reported. Progress towards the synthesis of conduritol systems featuring studies on the ring-closing metathesis reaction is also described.
Supervisor: Not available Sponsor: Not available
Qualification Name: Thesis (Ph.D.) Qualification Level: Doctoral
EThOS ID:  DOI: Not available