Studies towards low oxidation state taxanes
Publication Date
August 2, 2022
Creator
Abstract
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.
Item Type
ethesis
Thesis Type
MRes
Supervisors
Keywords
Subjects (LC)
Associated Schools / Departments
School of Chemistry
eprints ID
67433
UoN Repository URI
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Final Thesis -ready for submission 08012022.pdf
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Full-text
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