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This thesis addresses two fundamental areas in contemporary organic chemistry: synthesis of natural products and catalytic asymmetric synthesis. Firstly, a new methodology, developed by our research group, which allows the asymmetric synthesis of lactones, a structural unit ubiquitous in natural products, was utilised in the synthesis of a number of natural product analogues that showed significant biological activity. Secondly, the development of a catalytic asymmetric synthesis of a key structural motif present in a number of natural products and pharmaceuticals was accomplished. During the course of this work we discovered dual stereocontrol, which is significant because it allows the configuration of a new stereocentre to be controlled by a simple change of proton source.

Chemistry. --- Organic Chemistry. --- Catalysis. --- Medicinal Chemistry. --- Chemistry, Organic. --- Biochemistry. --- Chimie --- Chimie organique --- Biochimie --- Catalyse --- Chemistry --- Physical Sciences & Mathematics --- Biochemistry --- Asymmetric synthesis. --- Biosynthesis. --- Ketones. --- Diketones --- Biological synthesis --- Synthesis, Biological --- Asymmetric induction --- Induction, Asymmetric --- Synthesis, Asymmetric --- Organic chemistry. --- Medicinal chemistry. --- Biochemical engineering --- Organic compounds --- Biochemical templates --- Asymmetry (Chemistry) --- Oxo compounds --- Ketoacidosis --- Ketonuria --- Synthesis --- Organic chemistry --- Biological chemistry --- Chemical composition of organisms --- Organisms --- Physiological chemistry --- Biology --- Medical sciences --- Activation (Chemistry) --- Chemistry, Physical and theoretical --- Surface chemistry --- Composition --- Synthetic biology --- Chemistry, Medical and pharmaceutical --- Chemistry, Pharmaceutical --- Drug chemistry --- Drugs --- Medical chemistry --- Medicinal chemistry --- Pharmacochemistry