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Title: Studies towards the synthesis of the cladiellane oxacycles
Author: Davidson, J. E. P.
Awarding Body: University of Cambridge
Current Institution: University of Cambridge
Date of Award: 1997
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This dissertation details synthetic efforts towards the cladiellanes - metabolites isolated from certain species of coral. Chapter One is a comprehensive review of the area, covering the literature up until July 1997. Chapter Two describes preliminary investigations into the use of a synthetic strategy that would rely on the anionic oxy-Cope rearrangement for the formation of the cladiellane skeleton. This route was found to be impracticable, leading to the investigation of a new strategy relying on an intramolecular Diels-Alder reaction as the key step. Chapter Three discusses this new route, with the elaboration of the 9-membered lactone 3.7 to the tricyclic model-cladiellanes 3.19a and 3.19b (Scheme a). The key intramolecular Diels-Alder reaction was found to proceed in tandem with the preceding Wittig reaction, which was used to install the α,β-unsaturated methyl ketone dienophile functionality. The diastereometric products 3.19a and 3.19b were obtained in excellent yield over the two step process. During the course of these synthetic endeavours, novel methodology for the formation of ketene acetal Claisen rearrangement precursors was developed. Chapter Four describes the development of a tandem cyclic-carbonate methylenation/Claisen rearrangement strategy for the formation of 9-membered lactones, culminating in the synthesis of the highly functionalised lactone 4.45a (Scheme b).
Supervisor: Not available Sponsor: Not available
Qualification Name: Thesis (Ph.D.) Qualification Level: Doctoral
EThOS ID:  DOI: Not available