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Title: The total synthesis of the protein phosphatase inhibitor okadaic acid
Author: Humphries, A. C.
Awarding Body: University of Cambridge
Current Institution: University of Cambridge
Date of Award: 1999
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This thesis is divided into seven chapters. The first is a brief discussion of the structure, regulation and rôle of the protein phosphatases in biological systems, with particular emphasis on the important contribution made by the protein phosphatase inhibitor okadaic acid. The second chapter is a review of published synthetic work towards okadaic acid by other research groups. Chapter three begins with a brief review of some synthetic strategies towards the spiroketal unit. The general approach adopted within these laboratories for the total synthesis of okadaic acid is then described, with disconnections giving three distinct spiroketal units; followed by the synthesis of the central fragment. The fourth chapter describes the novel, intermolecular C-glycosylation of a 2-oxy substituted glycosyl sulfone. The application of this methodology to the introduction of a formyl unit into the anomeric position of the central spiroketal fragment is then described. Chapter five details a novel strategy towards the synthesis of the C15-C38 portion of okadaic acid, using the C-glycosylation methodology for the direct coupling of the C14-C26 and the C27-C38 fragments. It also contains a brief summary of the synthesis of the C27-C38 fragment from these laboratories. Chapter six begins with a review of the synthesis of the C1-C14 fragment from these laboratories. The coupling of the two advanced fragments is then detailed, together with the completion of the total synthesis.
Supervisor: Not available Sponsor: Not available
Qualification Name: Thesis (Ph.D.) Qualification Level: Doctoral
EThOS ID:  DOI: Not available