| Summary: | This thesis outlines work towards the optimisation and production of taxadienone, a useful precursor to the low oxidation state taxanes and a member of the taxane family of natural products, through synthetic chemistry.
Chapter I Introduces the taxane family of natural products, their biosynthesis, biological activities and extraction.
Chapter II describes our synthesis of taxadienone, using carbon building blocks from a sustainable source. We started our work with the formation of the C ring via an acid catalysed cyclisation of a polyene derived from the natural product, E/Z farnesol. A single isomer of farnesol was also used to study its effect on the diastereoselectivity of the cyclised product. Cyclisation was followed by the use of a novel indium-Reformatsky reaction to form a -lactone which subsequently underwent decarboxylation to form a tetra-substituted diene. This was followed by the well-established Diels-Alder approach to construct taxadienone.
Chapter III provides an experimental section that gives detailed procedures and full characterisation data for the novel compounds discussed in the results and discussion.
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