Studies towards the total synthesis of simonsol A
Neolignans are secondary metabolites found in plants from the genus Illicium and investigations into their bioactivity have shown them to possess medicinal properties. Dunnianol, a sesquineolignan, has shown neurotrophic activity in the promotion of neurite outgrowth. We hypothesised that the biosyn...
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| Format: | Thesis (University of Nottingham only) |
| Language: | English |
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2021
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| Online Access: | https://eprints.nottingham.ac.uk/65597/ |
| _version_ | 1848800246722723840 |
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| author | Boden, Grace |
| author_facet | Boden, Grace |
| author_sort | Boden, Grace |
| building | Nottingham Research Data Repository |
| collection | Online Access |
| description | Neolignans are secondary metabolites found in plants from the genus Illicium and investigations into their bioactivity have shown them to possess medicinal properties. Dunnianol, a sesquineolignan, has shown neurotrophic activity in the promotion of neurite outgrowth. We hypothesised that the biosynthesis of simonsol A is derived from dunnianol and this report focusses on the comparison between the two compounds and describes the synthesis towards simonsol A. An intermediate towards the synthesis of simonsol A was prepared through a microwave-assisted Suzuki-Miyaura cross-coupling reaction, followed by allylation of the phenolic core in 50% yield over 4 steps. Computational studies of the relative energies for the interconversion provide strong evidence towards the newly proposed biosynthesis of simonsol A. The energy barrier of the Claisen rearrangement was found to be 45.6 kcal/mol and for the Cope rearrangement, 32.5 Kcal/mol. |
| first_indexed | 2025-11-14T20:48:31Z |
| format | Thesis (University of Nottingham only) |
| id | nottingham-65597 |
| institution | University of Nottingham Malaysia Campus |
| institution_category | Local University |
| language | English |
| last_indexed | 2025-11-14T20:48:31Z |
| publishDate | 2021 |
| recordtype | eprints |
| repository_type | Digital Repository |
| spelling | nottingham-655972023-08-04T04:30:45Z https://eprints.nottingham.ac.uk/65597/ Studies towards the total synthesis of simonsol A Boden, Grace Neolignans are secondary metabolites found in plants from the genus Illicium and investigations into their bioactivity have shown them to possess medicinal properties. Dunnianol, a sesquineolignan, has shown neurotrophic activity in the promotion of neurite outgrowth. We hypothesised that the biosynthesis of simonsol A is derived from dunnianol and this report focusses on the comparison between the two compounds and describes the synthesis towards simonsol A. An intermediate towards the synthesis of simonsol A was prepared through a microwave-assisted Suzuki-Miyaura cross-coupling reaction, followed by allylation of the phenolic core in 50% yield over 4 steps. Computational studies of the relative energies for the interconversion provide strong evidence towards the newly proposed biosynthesis of simonsol A. The energy barrier of the Claisen rearrangement was found to be 45.6 kcal/mol and for the Cope rearrangement, 32.5 Kcal/mol. 2021-08-04 Thesis (University of Nottingham only) NonPeerReviewed application/pdf en cc_by https://eprints.nottingham.ac.uk/65597/1/Studies%20toward%20the%20total%20synthesis%20of%20simonsol%20A%20corrections.pdf Boden, Grace (2021) Studies towards the total synthesis of simonsol A. MRes thesis, University of Nottingham. neolignans metabolites therapeutics |
| spellingShingle | neolignans metabolites therapeutics Boden, Grace Studies towards the total synthesis of simonsol A |
| title | Studies towards the total synthesis of simonsol A |
| title_full | Studies towards the total synthesis of simonsol A |
| title_fullStr | Studies towards the total synthesis of simonsol A |
| title_full_unstemmed | Studies towards the total synthesis of simonsol A |
| title_short | Studies towards the total synthesis of simonsol A |
| title_sort | studies towards the total synthesis of simonsol a |
| topic | neolignans metabolites therapeutics |
| url | https://eprints.nottingham.ac.uk/65597/ |