Synthesis of the ABC fragment of pectenotoxin-4
<p>This thesis details the application of two synthetic methodologies, developed by the Donohoe group, to the synthesis of the ABC fragment of pectenotoxin-4, a macrolide marine natural product that consists of 19 stereogenic centres, three tetrahydrofuran rings, one spiroketal and one bicycli...
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| Format: | Thesis |
| Language: | English |
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2012
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| _version_ | 1817931971056107520 |
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| author | Lipinski, RM |
| author2 | Donohoe, T |
| author_facet | Donohoe, T Lipinski, RM |
| author_sort | Lipinski, RM |
| collection | OXFORD |
| description | <p>This thesis details the application of two synthetic methodologies, developed by the Donohoe group, to the synthesis of the ABC fragment of pectenotoxin-4, a macrolide marine natural product that consists of 19 stereogenic centres, three tetrahydrofuran rings, one spiroketal and one bicyclic ketal embedded within a 26-membered macrocycle.</p> <p>Pivotal to the developed synthetic route was the utilisation of an unprecedented cascade osmium catalysed oxidative cyclisation for the construction of two THF rings (the BC ring system). After successfully developing a model system for the synthesis of the AB anomeric 6,5 spiroketal, which involved the employment of a hydride shift initiated oxo carbenium ion formation followed by intramolecular spiroketalisation, the developed system was then applied to the fully elaborated synthesis of the ABC fragment.</p> <p>The synthesis of the ABC fragment of pectenotoxin-4 was completed in 20 linear steps, with an overall yield of 3.3%.</p> |
| first_indexed | 2024-03-06T18:57:09Z |
| format | Thesis |
| id | oxford-uuid:123bf4c1-844a-492a-abdb-f7555719d7ff |
| institution | University of Oxford |
| language | English |
| last_indexed | 2024-12-09T03:30:29Z |
| publishDate | 2012 |
| record_format | dspace |
| spelling | oxford-uuid:123bf4c1-844a-492a-abdb-f7555719d7ff2024-12-01T13:50:53ZSynthesis of the ABC fragment of pectenotoxin-4Thesishttp://purl.org/coar/resource_type/c_db06uuid:123bf4c1-844a-492a-abdb-f7555719d7ffOrganic synthesisSynthetic organic chemistryNatural productsOrganic chemistryHeterocyclic chemistryAsymmetric catalysisEnglishOxford University Research Archive - Valet2012Lipinski, RMDonohoe, T<p>This thesis details the application of two synthetic methodologies, developed by the Donohoe group, to the synthesis of the ABC fragment of pectenotoxin-4, a macrolide marine natural product that consists of 19 stereogenic centres, three tetrahydrofuran rings, one spiroketal and one bicyclic ketal embedded within a 26-membered macrocycle.</p> <p>Pivotal to the developed synthetic route was the utilisation of an unprecedented cascade osmium catalysed oxidative cyclisation for the construction of two THF rings (the BC ring system). After successfully developing a model system for the synthesis of the AB anomeric 6,5 spiroketal, which involved the employment of a hydride shift initiated oxo carbenium ion formation followed by intramolecular spiroketalisation, the developed system was then applied to the fully elaborated synthesis of the ABC fragment.</p> <p>The synthesis of the ABC fragment of pectenotoxin-4 was completed in 20 linear steps, with an overall yield of 3.3%.</p> |
| spellingShingle | Organic synthesis Synthetic organic chemistry Natural products Organic chemistry Heterocyclic chemistry Asymmetric catalysis Lipinski, RM Synthesis of the ABC fragment of pectenotoxin-4 |
| title | Synthesis of the ABC fragment of pectenotoxin-4 |
| title_full | Synthesis of the ABC fragment of pectenotoxin-4 |
| title_fullStr | Synthesis of the ABC fragment of pectenotoxin-4 |
| title_full_unstemmed | Synthesis of the ABC fragment of pectenotoxin-4 |
| title_short | Synthesis of the ABC fragment of pectenotoxin-4 |
| title_sort | synthesis of the abc fragment of pectenotoxin 4 |
| topic | Organic synthesis Synthetic organic chemistry Natural products Organic chemistry Heterocyclic chemistry Asymmetric catalysis |
| work_keys_str_mv | AT lipinskirm synthesisoftheabcfragmentofpectenotoxin4 |