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Title: Development of a dithiane-Julia olefination reaction : towards the synthesis of callipeltoside A
Author: Gold, J. B.
Awarding Body: University of Cambridge
Current Institution: University of Cambridge
Date of Award: 2008
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This doctoral thesis is divided into three sections: Part A, Part B and Part C. Part A is subdivided further into three chapters. In the first of these, an overview of the Julia olefination reaction process as well as its variants is provided, followed by a short description of the application of dithiane methodology in natural product synthesis. The second chapter describes the development of a new methodology based on Julia olefination of substrates derived from dithiane and dithiolane sulfones. Summary and conclusions then follow in chapter three. Part B of this thesis is also subdivided into three sections. The first chapter focuses on the discovery of the callipeltoside natural product family and in this context, structure elucidation and previous total syntheses of callipeltoside A are described. The second chapter outlines the successful synthesis of gram quantities of the crucial aldehyde fragment for the Ley group callipeltoside A synthesis using the double addition of dithiols to ynones developed within the group. Then a preliminary study of the coupling of this key intermediate with a diverse range of vinyl iodide fragments en route to callipeltoside A is described. Full summary, conclusions and details of future work towards completion of the synthesis of calipeltoside A are provided in the third chapter. Finally, a detailed description of experimental procedures and full analytical characterisation data are provided in Part C of this thesis.
Supervisor: Not available Sponsor: Not available
Qualification Name: Thesis (Ph.D.) Qualification Level: Doctoral
EThOS ID:  DOI: Not available