Higson, Sally; (2017) Sustainable Approaches to the Synthesis of Aromatic Compounds and α-Hydroxyketones. Doctoral thesis (Ph.D), UCL (University College London).

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Abstract

The unifying theme of this thesis is a sustainable approach to synthetic chemistry, focussing on two areas; the synthesis of aromatic compounds from biomass-derived furfural derivatives using environmentally friendly methodology, and the synthesis of α-hydroxyketones by expanding the substrate scope of transketolase enzymes by medium throughput mutant screening. Chapter I gives an overview of the principles and importance of sustainability in synthetic chemistry and presents a broad discussion of biomass sources and uses, the use of water as a solvent, and enzymatic catalysis in organic synthesis. Chapter II discusses the production of furfural derivatives from biomass, including the potential role of sugar beet pulp as a feedstock, and an overview of furfurals in synthesis. A new route to substituted benzene rings from furfurals via a three-step, one-pot cascade in water is then described, its scope explored, and an intramolecular variant developed. A ‘Design of Experiment’ optimisation of a furfural Michael addition is also presented. Chapter III concerns the reactivity and potential uses of the phthalimide hydrazones produced by the methodology introduced in Chapter II, presenting an overview of potential downstream products, a broad investigation of functional group manipulation, and a new synthetic route to a poly(ADP-ribose) ribose polymerase inhibitor and substituted phthalocyanines. Chapter IV explores the use of transketolase enzymes in the synthesis of α-hydroxyketones, investigating the role of enzyme variants in enhancing the acceptance of previously unreported non-natural keto-acid donor substrates. The development of a medium throughput methodology and its application in enzyme mutant screening is described. Chapter V gives a summary of the research carried out, presents some general conclusions, and describes future work, and Chapter VI contains the details of experimental procedures and compound characterisation for the results discussed in Chapters II-IV.

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