Bioinspired Synthesis of Illicium-Derived Neolignans and their Neurological Activity
Illicium-derived neolignans present a wealth of structurally diverse species that arise initially from the oxidative phenolic coupling of common unit chavicol whereby it is proposed that intermediates can also undergo oxa-1,4-additions, oxidations, and dehydrating transformations. More recently, Ill...
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| Format: | Thesis (University of Nottingham only) |
| Language: | English English |
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2021
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| Online Access: | https://eprints.nottingham.ac.uk/64407/ |
| _version_ | 1848800129581056000 |
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| author | Arnold, Robert |
| author_facet | Arnold, Robert |
| author_sort | Arnold, Robert |
| building | Nottingham Research Data Repository |
| collection | Online Access |
| description | Illicium-derived neolignans present a wealth of structurally diverse species that arise initially from the oxidative phenolic coupling of common unit chavicol whereby it is proposed that intermediates can also undergo oxa-1,4-additions, oxidations, and dehydrating transformations. More recently, Illicium-derived neolignans have been tested for their neurological benefits in the promotion of growth and protection of developing neurons.
This thesis presents a bioinspired approach for the total synthesis of simonsol C, simonsol F (previously unnamed) and simonsol G (previously unnamed), as well as their respective biomimetic transformations to simonsinol, macranthol and honokiol via plausible hydroxydienone intermediates. From simonsol F, the total synthesis of fargenin, simonsol E, simonsin A and two further possibly over-looked natural products epi-simonsol E and epi-simonsin A are described. Studies towards the synthesis of two possible diastereoisomers of fargenone A, “bowl” and “ladder” are presented. Efforts have begun towards an enantioselective synthesis of simonsol F. Illicium-derived neolignans, intermediates from synthesis and purposefully modified derivatives have been tested in an SAR study on the promotion of axon growth of primary cultured mouse cortical neurons. |
| first_indexed | 2025-11-14T20:46:39Z |
| format | Thesis (University of Nottingham only) |
| id | nottingham-64407 |
| institution | University of Nottingham Malaysia Campus |
| institution_category | Local University |
| language | English English |
| last_indexed | 2025-11-14T20:46:39Z |
| publishDate | 2021 |
| recordtype | eprints |
| repository_type | Digital Repository |
| spelling | nottingham-644072025-02-28T15:10:47Z https://eprints.nottingham.ac.uk/64407/ Bioinspired Synthesis of Illicium-Derived Neolignans and their Neurological Activity Arnold, Robert Illicium-derived neolignans present a wealth of structurally diverse species that arise initially from the oxidative phenolic coupling of common unit chavicol whereby it is proposed that intermediates can also undergo oxa-1,4-additions, oxidations, and dehydrating transformations. More recently, Illicium-derived neolignans have been tested for their neurological benefits in the promotion of growth and protection of developing neurons. This thesis presents a bioinspired approach for the total synthesis of simonsol C, simonsol F (previously unnamed) and simonsol G (previously unnamed), as well as their respective biomimetic transformations to simonsinol, macranthol and honokiol via plausible hydroxydienone intermediates. From simonsol F, the total synthesis of fargenin, simonsol E, simonsin A and two further possibly over-looked natural products epi-simonsol E and epi-simonsin A are described. Studies towards the synthesis of two possible diastereoisomers of fargenone A, “bowl” and “ladder” are presented. Efforts have begun towards an enantioselective synthesis of simonsol F. Illicium-derived neolignans, intermediates from synthesis and purposefully modified derivatives have been tested in an SAR study on the promotion of axon growth of primary cultured mouse cortical neurons. 2021-08-04 Thesis (University of Nottingham only) NonPeerReviewed application/pdf en arr https://eprints.nottingham.ac.uk/64407/1/Neolignans%20-%20Robert%20Arnold.pdf application/pdf en arr https://eprints.nottingham.ac.uk/64407/2/Neolignans%20-%20Robert%20Arnold%20-%20Supporting%20NMR%20Spectra.pdf Arnold, Robert (2021) Bioinspired Synthesis of Illicium-Derived Neolignans and their Neurological Activity. PhD thesis, University of Nottingham. neolignans lignans biosynthesis |
| spellingShingle | neolignans lignans biosynthesis Arnold, Robert Bioinspired Synthesis of Illicium-Derived Neolignans and their Neurological Activity |
| title | Bioinspired Synthesis of Illicium-Derived Neolignans and their Neurological Activity |
| title_full | Bioinspired Synthesis of Illicium-Derived Neolignans and their Neurological Activity |
| title_fullStr | Bioinspired Synthesis of Illicium-Derived Neolignans and their Neurological Activity |
| title_full_unstemmed | Bioinspired Synthesis of Illicium-Derived Neolignans and their Neurological Activity |
| title_short | Bioinspired Synthesis of Illicium-Derived Neolignans and their Neurological Activity |
| title_sort | bioinspired synthesis of illicium-derived neolignans and their neurological activity |
| topic | neolignans lignans biosynthesis |
| url | https://eprints.nottingham.ac.uk/64407/ |