Towards the synthesis of the ABC fragment of pectenotoxin-4
<p>This thesis details the optimisation and development to the synthesis of the ABC fragment of pectenotoxin-4, a 26-membered macrolide marine natural product bearing 19 stereogenic centres, three tetrahydrofuran rings, one spiroketal and one bicyclic ketal.</p> <p><b>Introdu...
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| Format: | Thesis |
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2016
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| _version_ | 1826259672690065408 |
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| author | Yang, X |
| author2 | Donohoe, T |
| author_facet | Donohoe, T Yang, X |
| author_sort | Yang, X |
| collection | OXFORD |
| description | <p>This thesis details the optimisation and development to the synthesis of the ABC fragment of pectenotoxin-4, a 26-membered macrolide marine natural product bearing 19 stereogenic centres, three tetrahydrofuran rings, one spiroketal and one bicyclic ketal.</p> <p><b>Introduction</b></p> <p>This section briefly discusses the isolation, structure elucidation, and biological activity of penctenotoxins, along with a review of previous synthetic efforts on the pectenotoxin family, especially the ABC fragment. It also summarises our group’s work in pursuing the total synthesis of this compound.</p> <p><b>Results and Discussion</b></p> <p>This section details synthetic efforts to improve the overall yield of the ABC fragment. In particular, it contains the optimisation of a low yield Carreira alkynylation reaction and a revised protecting group strategy to allow orthogonal deprotection on the ABC fragment for further elaborations. The revised route for the ABC fragment of pectenotoxin-4 contains 21 longest linear steps (27 steps in total) from D-mannitol with an overall yield of 2.1% (on average 83% per step).</p> |
| first_indexed | 2024-03-06T18:53:32Z |
| format | Thesis |
| id | oxford-uuid:110cddcd-a7c2-453d-94e5-e3c5b7e2ae14 |
| institution | University of Oxford |
| last_indexed | 2024-03-06T18:53:32Z |
| publishDate | 2016 |
| record_format | dspace |
| spelling | oxford-uuid:110cddcd-a7c2-453d-94e5-e3c5b7e2ae142022-03-26T10:00:00ZTowards the synthesis of the ABC fragment of pectenotoxin-4Thesishttp://purl.org/coar/resource_type/c_db06uuid:110cddcd-a7c2-453d-94e5-e3c5b7e2ae14ORA Deposit2016Yang, XDonohoe, T<p>This thesis details the optimisation and development to the synthesis of the ABC fragment of pectenotoxin-4, a 26-membered macrolide marine natural product bearing 19 stereogenic centres, three tetrahydrofuran rings, one spiroketal and one bicyclic ketal.</p> <p><b>Introduction</b></p> <p>This section briefly discusses the isolation, structure elucidation, and biological activity of penctenotoxins, along with a review of previous synthetic efforts on the pectenotoxin family, especially the ABC fragment. It also summarises our group’s work in pursuing the total synthesis of this compound.</p> <p><b>Results and Discussion</b></p> <p>This section details synthetic efforts to improve the overall yield of the ABC fragment. In particular, it contains the optimisation of a low yield Carreira alkynylation reaction and a revised protecting group strategy to allow orthogonal deprotection on the ABC fragment for further elaborations. The revised route for the ABC fragment of pectenotoxin-4 contains 21 longest linear steps (27 steps in total) from D-mannitol with an overall yield of 2.1% (on average 83% per step).</p> |
| spellingShingle | Yang, X Towards the synthesis of the ABC fragment of pectenotoxin-4 |
| title | Towards the synthesis of the ABC fragment of pectenotoxin-4 |
| title_full | Towards the synthesis of the ABC fragment of pectenotoxin-4 |
| title_fullStr | Towards the synthesis of the ABC fragment of pectenotoxin-4 |
| title_full_unstemmed | Towards the synthesis of the ABC fragment of pectenotoxin-4 |
| title_short | Towards the synthesis of the ABC fragment of pectenotoxin-4 |
| title_sort | towards the synthesis of the abc fragment of pectenotoxin 4 |
| work_keys_str_mv | AT yangx towardsthesynthesisoftheabcfragmentofpectenotoxin4 |