Use this URL to cite or link to this record in EThOS: http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.730229
Title: Synthesis of the CDE & EFG ring systems of pectenotoxin-4
Author: Liu, Yifan
ISNI:       0000 0004 6495 6562
Awarding Body: University of Oxford
Current Institution: University of Oxford
Date of Award: 2016
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Abstract:
This thesis explores new synthetic routes for the formation of CDE & EFG fragments of pectenotoxin-4. Chapter 1: Introduction and Previous Work: 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. Chapter 2: Synthesis of the E Ring Fragment of Pectenotoxin-4: The synthesis of the E ring fragment is discussed. Key reactions include Negishi coupling and osmium mediated oxidative cyclisation. Chapter 3: First Generation Strategy for the Synthesis of the D ring: A simple model towards the D ring core was completed using alkyne-epoxide opening strategy. The application on a more sophisticated system was tested. Chapter 4: Second Generation Strategy for the Synthesis of the D ring: Sonogashira coupling was successfully tested as key step to unite two coupling partners; and further functionalisation towards the D ring skeleton was studied. Chapter 5: Third Generation Strategy for the Synthesis of the D ring: 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. Chapter 6: Synthesis of EFG Fragment of Pectenotoxin-4: 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. Chapter 7: Experimental: Full experimental procedures and characterisation of compounds are reported.
Supervisor: Donohoe, Timothy Sponsor: China Scholarship Council ; Eli Lilly and Co
Qualification Name: Thesis (Ph.D.) Qualification Level: Doctoral
EThOS ID: uk.bl.ethos.730229  DOI: Not available
Keywords: total synthesis ; organic chemistry ; synthetic organic chemistry ; pectenotoxin
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