Morrell, J.M.; (2008) Synthesis of 4h-pyran-4-ones, other cyclic oxygenated systems and related modelling studies. Doctoral thesis , University of London.

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Abstract

The aim of the project was to investigate the use of mercury mediated cyclisation reactions resulting in the generation of 2,3-dihydropyran-4//-one and 3(2//)-furanone systems. Chapter one discusses the general synthesis of dihydropyranones and furanones. The chapter continues and focuses upon the use of a mercury-mediated cyclisation strategy in the synthesis of 2,3-dihydropyran-4-ones and 3(2//)-mranones. Finally the chapter describes efforts to utilise a mercury-mediated cyclisation strategy to synthesise useful synthetic intermediates. Chapter two is focused upon protein phosphorylation inhibitors, and begins by discussing the processes of protein phosphorylation and compounds which inhibit the process. The chapter focuses on fostriecin and phospholine compounds, and discusses efforts to synthesise key fragments of the compounds using a mercury-mediated cyclisation protocol. Chapter three describes histone deacetylase inhibitors, and their mode of action. The use of computational models to predict and rationalise inhibitor activity is discussed. A small selection of HDAC inhibitors are used to demonstrate the Autodock system in predicting inhibitory activity. A previously unknown compound is synthesized, and inhibitory properties compared to those predicted by the Autodock system. Chapter four discusses efforts to synthesise the spiroketal subunit of (-)-calyculin A. Initially a mercury-mediated cyclisation strategy is presented, detailing the preparation of two key fragments which are combined to form a key scaffold used in the cyclisation strategy. The chapter then describes the use of auxiliary fragments in attempts to generate the spiroketal fragment.

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