Maltman, Beatrice Angela; (2003) Studies towards a total synthesis of colchicine. Doctoral thesis (Ph.D), UCL (University College London).

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Abstract

This thesis describes a novel strategic approach towards the synthesis of colchicine which involves the use of the transition metal catalysed [5+2] cycloaddition reaction. The thesis is divided into three chapters. The first introductory chapter presents an overview of colchicine, with particular attention being focused on the isolation, structure, biological properties and biosynthesis of the natural product, together with a thorough account of previous synthetic approaches. Moreover, since the key reaction in our synthetic approach involves the exploitation of the transition metal catalysed [5+2] cycloaddition reaction, a detailed review into the recent developments and uses of this reaction is presented. In the second chapter, synthetic approaches are described for the preparation of two structurally different alkynyl-vinylcyclopropanes which are required for exploitation of the intramolecular variant of the transition metal mediated [5+2] cycloaddition, this strategy being selected to achieve concomitant formation of both seven-membered rings and also avoiding the problematic methylation of a free tropolone unit. Detailed accounts of the successful synthetic routes to both of these potential cyclisation precursors are presented and discussed. In the event however, formation of the tricyclic skeleton by a variety of metal catalysed [5+2] cycloaddition protocols proved elusive. The third chapter provides a formal description of the experimental procedures and results obtained.

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