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Title: Synthesis of the C(16)-C(28) CD spiroketal fragment of spongistatin 1
Author: Hook, D. F.
Awarding Body: University of Cambridge
Current Institution: University of Cambridge
Date of Award: 2003
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This thesis is divided into 7 chapters. Chapter 1 describes the isolation and structure determination of the spongistatins. The biological activity of these molecules is discussed along with the development of pharmacophores. The relevance of the anomeric effect is also outlined. Chapter 2 reviews the published syntheses of the CD spiroketal fragment, highlighting the important steps in each. Chapter 3 details the current strategy within our group towards a total synthesis of spongistatin 1. An existing synthesis of a CD spiroketal-containing fragment is presented along with the need for an improved synthesis, which shall form the basis of the following two chapters. Chapter 4 outlines a first generation approach to the CD spiroketal fragment based on the spiroketalisation of a b-keto-1,3-dithiane. Transformation to reveal functionalised CD spiroketal-based compounds are presented. Chapter 5 describes a second generation synthesis, drawing on the chemistry developed in Chapter 4. Successful elaboration to the desired C(16)-C(28) CD spiroketal fragment is discussed. Chapter 6 reveals a complementary approach to the AB spiroketal fragment along with a coupling to the CD spiroketal unit. Progress towards the C(29)-C(51) fragment is presented, along with the proposed final steps to assemble spongistatin 1. Details of a unified approach to assemble the Northern Fragment is also outlined. Chapter 7 provides a detailed account of the experimental procedures.
Supervisor: Not available Sponsor: Not available
Qualification Name: Thesis (Ph.D.) Qualification Level: Doctoral
EThOS ID:  DOI: Not available