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Title: Novel methods for 18F-radiolabelling
Author: Calderwood, Samuel
ISNI:       0000 0004 6494 6946
Awarding Body: University of Oxford
Current Institution: University of Oxford
Date of Award: 2016
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The expansion of [18F]-radiolabelling methodologies is vital for the advancement of Positron Emission Tomography (PET) as a medical imaging tool. Novel protocols will simplify access to current PET tracers and allow development of original tracers, potentially enhancing the imaging quality or permit imaging of a wider range of clinical problems. A general introduction is presented in Chapter 1, covering PET, application of fluorine-19 in the pharmaceutical industry, the production of fluorine-18 and the current state-of -art for [18F]-radiolabelling. The results chapters are divided in to two parts; Part 1 (Chapters 2 - 4) concern the synthesis of [18F]fluoroarenes and Part II (Chapters 5 and 6) discuss diversity oriented radiofluorination techniques, targeting novel [18F]motifs. In Part I, Chapter 2 describes the use of hypervalent iodine reagents to meditate an umpolung approach for fluorination and radiofluorination of N-arylsulfonamides and anilides. Chapter 3 again utilises hypervalent iodine reagents, but as spirocyclic iodonium(III) ylide precursors, being applied to semi-automated and automated microfluidic conditions. Chapter 4 discusses the development of conditions for the production and isolation of radiopharmaceuticals employing Cu(II)-mediated radiofluorination of aryl boronic pinacol esters. In Part II, Chapter 5 discusses the applicability of halogen exchange reactions to reach polyfluorinated motfis and Chapter 6 focuses on the application of a single diazo precursor to access three polyfluorinated motifs with single-step reactions. Finally, Chapter 7 provides experimental data for compounds discussed in this thesis.
Supervisor: Gouverneur, Véronique Sponsor: Medical Research Council
Qualification Name: Thesis (Ph.D.) Qualification Level: Doctoral
EThOS ID:  DOI: Not available
Keywords: Radiochemistry ; Radiofluorination ; Fluorine-18 ; Organic Chemistry ; Positron Emission Tomography