Adventures in natural product chemistry
Halichlorine, pinnaic acid and pinnarine are a novel family of marine alkaloids, characterised by their common 6-aza-spiro[4.5]decane ring system. First isolated in 1996 by Uemura et al, they have been shown to be biologically active with potential applications in the fields of inflammatory response...
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| Format: | Thesis (University of Nottingham only) |
| Language: | English |
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2020
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| Online Access: | https://eprints.nottingham.ac.uk/61452/ |
| _version_ | 1848799878438715392 |
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| author | Ward, Thomas E |
| author_facet | Ward, Thomas E |
| author_sort | Ward, Thomas E |
| building | Nottingham Research Data Repository |
| collection | Online Access |
| description | Halichlorine, pinnaic acid and pinnarine are a novel family of marine alkaloids, characterised by their common 6-aza-spiro[4.5]decane ring system. First isolated in 1996 by Uemura et al, they have been shown to be biologically active with potential applications in the fields of inflammatory response and tumor metastasis.
This project details the attempted total synthesis of the halichlorine family, focusing on the construction of the 6-aza-spiro[4.5]decane core ring system from cyclopentanone derivatives. Synthesis of the challenging C-14 and C-13 centers was achived diastereoselectively via Tsuji-Trost allylations. However, attempts to deliver the C-9 spirocyclic centre were met with failure. Exploration of secondary synthetic routes were also largely unsuccessful.
Secondary projects detail the attempted N-allylation of sulfinimines, aza-Heck cyclisations for the synthesis of anatoxin-a analogues and Synthetic methodology for the synthesis of renewable monomers from the seed oil derived fatty acid, vernolic acid. |
| first_indexed | 2025-11-14T20:42:40Z |
| format | Thesis (University of Nottingham only) |
| id | nottingham-61452 |
| institution | University of Nottingham Malaysia Campus |
| institution_category | Local University |
| language | English |
| last_indexed | 2025-11-14T20:42:40Z |
| publishDate | 2020 |
| recordtype | eprints |
| repository_type | Digital Repository |
| spelling | nottingham-614522025-02-28T15:02:30Z https://eprints.nottingham.ac.uk/61452/ Adventures in natural product chemistry Ward, Thomas E Halichlorine, pinnaic acid and pinnarine are a novel family of marine alkaloids, characterised by their common 6-aza-spiro[4.5]decane ring system. First isolated in 1996 by Uemura et al, they have been shown to be biologically active with potential applications in the fields of inflammatory response and tumor metastasis. This project details the attempted total synthesis of the halichlorine family, focusing on the construction of the 6-aza-spiro[4.5]decane core ring system from cyclopentanone derivatives. Synthesis of the challenging C-14 and C-13 centers was achived diastereoselectively via Tsuji-Trost allylations. However, attempts to deliver the C-9 spirocyclic centre were met with failure. Exploration of secondary synthetic routes were also largely unsuccessful. Secondary projects detail the attempted N-allylation of sulfinimines, aza-Heck cyclisations for the synthesis of anatoxin-a analogues and Synthetic methodology for the synthesis of renewable monomers from the seed oil derived fatty acid, vernolic acid. 2020-12-31 Thesis (University of Nottingham only) NonPeerReviewed application/pdf en arr https://eprints.nottingham.ac.uk/61452/1/Thomas%20Ward%20PhD%20thesis.pdf Ward, Thomas E (2020) Adventures in natural product chemistry. PhD thesis, University of Nottingham. Total synthesis Halichlorine Pinnarine Pinnaic acid |
| spellingShingle | Total synthesis Halichlorine Pinnarine Pinnaic acid Ward, Thomas E Adventures in natural product chemistry |
| title | Adventures in natural product chemistry |
| title_full | Adventures in natural product chemistry |
| title_fullStr | Adventures in natural product chemistry |
| title_full_unstemmed | Adventures in natural product chemistry |
| title_short | Adventures in natural product chemistry |
| title_sort | adventures in natural product chemistry |
| topic | Total synthesis Halichlorine Pinnarine Pinnaic acid |
| url | https://eprints.nottingham.ac.uk/61452/ |