Villa, Mathew V.J.
The design and synthesis of novel potential antimalarial compounds.
PhD thesis, University of Glasgow.
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The work contained in this thesis is split into two sections.
Each section covers a different biological pathway, its current importance as a potential
drug target, and the syntheses towards a selection of natural products and analogues
relevant to the pathway.
In Section A, the novel approach towards a new class of n-formyl amides is described.
Furthermore, this new methodology is used to generate the imide intermediate A1. This
imide is now considered a key intermediate in our synthesis of natural products CJ-15,801,
Pantothenate, and the first generation of analogues based on CJ-15,801.
This section also covers the potential scope for n-formyl imides in chemical synthesis in
Section B describes two novel approaches towards non-mevalonate pathway (MEP)
intermediates and inhibitors. The synthesis towards a previously unpublished 2,2-dimethyl
MEP analogue, is described alongside the attempted generation MEP. The methodology
described herein shows the use of Neighbouring Group Participation in intramolecular
opening of epoxides, and how this can be applied to the generation of analogues.
Above all, the aim of this thesis is to open up new synthetic strategies towards potential
inhibitors for individual biosynthetic pathways.
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