Synthesis of the CDE & EFG ring systems of pectenotoxin-4
<p>This thesis explores new synthetic routes for the formation of CDE & EFG fragments of pectenotoxin-4.</p> <b><p>Chapter 1: Introduction and Previous Work</p></b> <p>This chapter reviews the discovery and biological activities of members of the pec...
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| Format: | Thesis |
| Language: | English |
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2016
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| _version_ | 1826316103554433024 |
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| author | Liu, Y |
| author2 | Robertson, J |
| author_facet | Robertson, J Liu, Y |
| author_sort | Liu, Y |
| collection | OXFORD |
| description | <p>This thesis explores new synthetic routes for the formation of CDE & EFG fragments of pectenotoxin-4.</p> <b><p>Chapter 1: Introduction and Previous Work</p></b> <p>This chapter reviews the discovery and biological activities of members of the pectenotoxin family. Two previous total syntheses are discussed, and previous work regarding the synthesis of ABC, E and FG fragments within the group is introduced.</p> <b><p>Chapter 2: Synthesis of the E Ring Fragment of Pectenotoxin-4</p></b> <p>The synthesis of the E ring fragment is discussed. Key reactions include Negishi coupling and osmium mediated oxidative cyclisation.</p> <b><p>Chapter 3: First Generation Strategy for the Synthesis of the D ring</p></b> <p>A simple model towards the D ring core was completed using alkyne-epoxide opening strategy. The application on a more sophisticated system was tested.</p> <b><p>Chapter 4: Second Generation Strategy for the Synthesis of the D ring</p></b> <p>Sonogashira coupling was successfully tested as key step to unite two coupling partners; and further functionalisation towards the D ring skeleton was studied.</p> <b><p>Chapter 5: Third Generation Strategy for the Synthesis of the D ring</p></b> <p>The new strategy including a Lewis acid assisted coupling and mercury mediated hydration of alkyne sequence was completed on a simple model. The application on a more sophisticated system was tested.</p> <b><p>Chapter 6: Synthesis of EFG Fragment of Pectenotoxin-4</p></b> <p>Key Julia−Kocienski olefination between E ring fragment and FG ring fragment was examined. The further functionalisation of the resulting coupling product towards EFG fragment was finished.</p> <b><p>Chapter 7: Experimental</p></b> <p>Full experimental procedures and characterisation of compounds are reported.</p> |
| first_indexed | 2024-03-07T04:02:54Z |
| format | Thesis |
| id | oxford-uuid:c531f0b3-4961-43e6-b7aa-c273df89a16f |
| institution | University of Oxford |
| language | English |
| last_indexed | 2024-12-09T03:39:49Z |
| publishDate | 2016 |
| record_format | dspace |
| spelling | oxford-uuid:c531f0b3-4961-43e6-b7aa-c273df89a16f2024-12-06T08:01:57ZSynthesis of the CDE & EFG ring systems of pectenotoxin-4Thesishttp://purl.org/coar/resource_type/c_db06uuid:c531f0b3-4961-43e6-b7aa-c273df89a16fChemistry, OrganicEnglishORA Deposit2016Liu, YRobertson, JDonohoe, T<p>This thesis explores new synthetic routes for the formation of CDE & EFG fragments of pectenotoxin-4.</p> <b><p>Chapter 1: Introduction and Previous Work</p></b> <p>This chapter reviews the discovery and biological activities of members of the pectenotoxin family. Two previous total syntheses are discussed, and previous work regarding the synthesis of ABC, E and FG fragments within the group is introduced.</p> <b><p>Chapter 2: Synthesis of the E Ring Fragment of Pectenotoxin-4</p></b> <p>The synthesis of the E ring fragment is discussed. Key reactions include Negishi coupling and osmium mediated oxidative cyclisation.</p> <b><p>Chapter 3: First Generation Strategy for the Synthesis of the D ring</p></b> <p>A simple model towards the D ring core was completed using alkyne-epoxide opening strategy. The application on a more sophisticated system was tested.</p> <b><p>Chapter 4: Second Generation Strategy for the Synthesis of the D ring</p></b> <p>Sonogashira coupling was successfully tested as key step to unite two coupling partners; and further functionalisation towards the D ring skeleton was studied.</p> <b><p>Chapter 5: Third Generation Strategy for the Synthesis of the D ring</p></b> <p>The new strategy including a Lewis acid assisted coupling and mercury mediated hydration of alkyne sequence was completed on a simple model. The application on a more sophisticated system was tested.</p> <b><p>Chapter 6: Synthesis of EFG Fragment of Pectenotoxin-4</p></b> <p>Key Julia−Kocienski olefination between E ring fragment and FG ring fragment was examined. The further functionalisation of the resulting coupling product towards EFG fragment was finished.</p> <b><p>Chapter 7: Experimental</p></b> <p>Full experimental procedures and characterisation of compounds are reported.</p> |
| spellingShingle | Chemistry, Organic Liu, Y Synthesis of the CDE & EFG ring systems of pectenotoxin-4 |
| title | Synthesis of the CDE & EFG ring systems of pectenotoxin-4 |
| title_full | Synthesis of the CDE & EFG ring systems of pectenotoxin-4 |
| title_fullStr | Synthesis of the CDE & EFG ring systems of pectenotoxin-4 |
| title_full_unstemmed | Synthesis of the CDE & EFG ring systems of pectenotoxin-4 |
| title_short | Synthesis of the CDE & EFG ring systems of pectenotoxin-4 |
| title_sort | synthesis of the cde efg ring systems of pectenotoxin 4 |
| topic | Chemistry, Organic |
| work_keys_str_mv | AT liuy synthesisofthecdeefgringsystemsofpectenotoxin4 |