Studies towards low oxidation state taxanes
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 biosynthesi...
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| Format: | Thesis (University of Nottingham only) |
| Language: | English |
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2022
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| Online Access: | https://eprints.nottingham.ac.uk/67433/ |
| _version_ | 1848800419476668416 |
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| author | Sadia, Reema |
| author_facet | Sadia, Reema |
| author_sort | Sadia, Reema |
| building | Nottingham Research Data Repository |
| collection | Online Access |
| description | 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. |
| first_indexed | 2025-11-14T20:51:16Z |
| format | Thesis (University of Nottingham only) |
| id | nottingham-67433 |
| institution | University of Nottingham Malaysia Campus |
| institution_category | Local University |
| language | English |
| last_indexed | 2025-11-14T20:51:16Z |
| publishDate | 2022 |
| recordtype | eprints |
| repository_type | Digital Repository |
| spelling | nottingham-674332025-02-28T15:14:22Z https://eprints.nottingham.ac.uk/67433/ Studies towards low oxidation state taxanes Sadia, Reema 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. 2022-08-02 Thesis (University of Nottingham only) NonPeerReviewed application/pdf en cc_by https://eprints.nottingham.ac.uk/67433/1/Final%20Thesis%20-ready%20for%20submission%2008012022.pdf Sadia, Reema (2022) Studies towards low oxidation state taxanes. MRes thesis, University of Nottingham. Low oxidation state Taxanes |
| spellingShingle | Low oxidation state Taxanes Sadia, Reema Studies towards low oxidation state taxanes |
| title | Studies towards low oxidation state taxanes |
| title_full | Studies towards low oxidation state taxanes |
| title_fullStr | Studies towards low oxidation state taxanes |
| title_full_unstemmed | Studies towards low oxidation state taxanes |
| title_short | Studies towards low oxidation state taxanes |
| title_sort | studies towards low oxidation state taxanes |
| topic | Low oxidation state Taxanes |
| url | https://eprints.nottingham.ac.uk/67433/ |