Studies towards low oxidation state taxanes

Sadia, Reema (2022) Studies towards low oxidation state taxanes. MRes thesis, University of Nottingham.

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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: Thesis (University of Nottingham only) (MRes)
Supervisors: Hayes, Christopher
Keywords: Low oxidation state, Taxanes
Subjects: Q Science > QD Chemistry > QD241 Organic chemistry
Faculties/Schools: UK Campuses > Faculty of Science > School of Chemistry
Item ID: 67433
Depositing User: Sadia, Reema
Date Deposited: 02 Aug 2022 04:40
Last Modified: 02 Aug 2022 04:40
URI: http://eprints.nottingham.ac.uk/id/eprint/67433

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