A novel approach to the synthesis of the FG fragment of pectenotoxin-4
<p>The cobalt-catalysed oxidative cyclisation of 5-hydroxy alkenes has been demonstrated to be a powerful synthetic tool for the formation of trans-THFs with excellent diastereoselectivity. This thesis describes the utilisation of this methodology in the synthesis of the FG fragment of pecteno...
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| Format: | Thesis |
| Language: | English |
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2012
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| _version_ | 1826307494331285504 |
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| author | Luscombe, KN |
| author2 | Donohoe, TJ |
| author_facet | Donohoe, TJ Luscombe, KN |
| author_sort | Luscombe, KN |
| collection | OXFORD |
| description | <p>The cobalt-catalysed oxidative cyclisation of 5-hydroxy alkenes has been demonstrated to be a powerful synthetic tool for the formation of trans-THFs with excellent diastereoselectivity. This thesis describes the utilisation of this methodology in the synthesis of the FG fragment of pectenotoxin-4, allowing the scope of the reaction to be further explored.</p><p>Introduction: This section introduces the pectenotoxins, a family of structurally complex closed-chain polyether macrolides with promising biological activities. The isolation, structural elucidation, and biological properties of the pectenotoxins are reviewed, along with a summary of previous syntheses towards the FG fragment of pectenotoxin-4. In addition, the cobalt-catalysed oxidative cyclisation of 5-hydroxy alkenes and its application in synthesis is discussed.</p><p>Results and Discussion: An outline of the synthetic strategy employed in this project and details of the novel retrosynthesis of the C31-C40 fragment of pectenotoxin-4 is described. The synthetic studies carried out towards the synthesis of the FG fragment of pectenotoxin-4 are discussed in detail, with the exploitation of a cobalt-catalysed oxidative cyclisation as the key step to form the <em>trans</em>-THF F-ring. Overall, the FG fragment, which contains six stereogenic centres, was achieved in 18 total synthetic steps (13 longest linear sequence).</p> |
| first_indexed | 2024-03-07T07:03:54Z |
| format | Thesis |
| id | oxford-uuid:e434af14-cc0d-4ecf-b60e-2ed635e48fb8 |
| institution | University of Oxford |
| language | English |
| last_indexed | 2024-03-07T07:03:54Z |
| publishDate | 2012 |
| record_format | dspace |
| spelling | oxford-uuid:e434af14-cc0d-4ecf-b60e-2ed635e48fb82022-04-05T14:32:47ZA novel approach to the synthesis of the FG fragment of pectenotoxin-4Thesishttp://purl.org/coar/resource_type/c_db06uuid:e434af14-cc0d-4ecf-b60e-2ed635e48fb8Organic chemistryOrganic synthesisEnglishOxford University Research Archive - Valet2012Luscombe, KNDonohoe, TJ<p>The cobalt-catalysed oxidative cyclisation of 5-hydroxy alkenes has been demonstrated to be a powerful synthetic tool for the formation of trans-THFs with excellent diastereoselectivity. This thesis describes the utilisation of this methodology in the synthesis of the FG fragment of pectenotoxin-4, allowing the scope of the reaction to be further explored.</p><p>Introduction: This section introduces the pectenotoxins, a family of structurally complex closed-chain polyether macrolides with promising biological activities. The isolation, structural elucidation, and biological properties of the pectenotoxins are reviewed, along with a summary of previous syntheses towards the FG fragment of pectenotoxin-4. In addition, the cobalt-catalysed oxidative cyclisation of 5-hydroxy alkenes and its application in synthesis is discussed.</p><p>Results and Discussion: An outline of the synthetic strategy employed in this project and details of the novel retrosynthesis of the C31-C40 fragment of pectenotoxin-4 is described. The synthetic studies carried out towards the synthesis of the FG fragment of pectenotoxin-4 are discussed in detail, with the exploitation of a cobalt-catalysed oxidative cyclisation as the key step to form the <em>trans</em>-THF F-ring. Overall, the FG fragment, which contains six stereogenic centres, was achieved in 18 total synthetic steps (13 longest linear sequence).</p> |
| spellingShingle | Organic chemistry Organic synthesis Luscombe, KN A novel approach to the synthesis of the FG fragment of pectenotoxin-4 |
| title | A novel approach to the synthesis of the FG fragment of pectenotoxin-4 |
| title_full | A novel approach to the synthesis of the FG fragment of pectenotoxin-4 |
| title_fullStr | A novel approach to the synthesis of the FG fragment of pectenotoxin-4 |
| title_full_unstemmed | A novel approach to the synthesis of the FG fragment of pectenotoxin-4 |
| title_short | A novel approach to the synthesis of the FG fragment of pectenotoxin-4 |
| title_sort | novel approach to the synthesis of the fg fragment of pectenotoxin 4 |
| topic | Organic chemistry Organic synthesis |
| work_keys_str_mv | AT luscombekn anovelapproachtothesynthesisofthefgfragmentofpectenotoxin4 AT luscombekn novelapproachtothesynthesisofthefgfragmentofpectenotoxin4 |