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: | Disertacija |
| Jezik: | English |
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2016
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| Sažetak: | <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> |
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