Cayley, A.N.; (2007) Synthesis and photodegradation studies of analogues of the hop-derived iso-a-acids. Doctoral thesis , University of London.

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Abstract

This thesis describes the synthesis and photodegradation studies of some analogues of the isohumulones, a class of polycarbonyl organic compounds present in beer. Studies have been initiated in an attempt to elucidate the mechanism of the so called "sunstruck effect", a photodegradation reaction of the isohumulones which occurs in beer when it is left in sunlight. The first chapter of the thesis is concerned, primarily, with the biosynthesis and reactivity of the isohumulones and contains a brief review of literature methods for the synthesis of these compounds and their analogues, including descriptions of synthetic methods for the formation of the key functional groups present in these types of structures. The second chapter presents the results and gives a discussion of the research carried out. The production of some simple isohumulone analogues by the use of thioacetal anion chemistry is described, along with the results of investigations into the synthesis of isohumulone analogues via the ring contraction reaction of analogues of the natural product, humulone. Results of studies into the direct formation of polycarbonyl cyclopentanoids are also reported. This is followed by the results of preliminary photolysis studies carried out on the compounds synthesised. Chapter three of the thesis presents the conclusions which have been drawn from the work presented in chapter two and provides suggestions for possible directions of this research in the future. The final chapter provides a formal account of the experimental procedures developed during the work described in this thesis.

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