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Title: Synthesis of the ABC fragment of pectenotoxin-4
Author: Lipinski, Radoslaw Michal
ISNI:       0000 0004 2745 4205
Awarding Body: University of Oxford
Current Institution: University of Oxford
Date of Award: 2012
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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. 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. The synthesis of the ABC fragment of pectenotoxin-4 was completed in 20 linear steps, with an overall yield of 3.3%.
Supervisor: Donohoe, Timothy J. Sponsor: Dulverton Trust (Michael Wills Scholarship)
Qualification Name: Thesis (Ph.D.) Qualification Level: Doctoral
EThOS ID:  DOI: Not available
Keywords: Heterocyclic chemistry ; Asymmetric catalysis ; Organic chemistry ; Organic synthesis ; Synthetic organic chemistry ; catalysis ; cyclization ; natural products ; pectenotoxin ; spiroketals