UBC Theses and Dissertations

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UBC Theses and Dissertations

An aspect of pyrone chemistry Webster, Godfrey Robin Barrie

Abstract

Since 1893, acetate has been regarded as a very important precursor of naturally occurring phenolic compounds. Although intensive work has been directed at the complete elucidation of this biogenetic pathway, a satisfactory method has yet to be devised for the synthesis of the polyketide chains proposed as intermediates in the acetate scheme. Labelling studies with such compounds would provide information regarding their intermediate role in the acetate route to aromatic compounds. Efforts to date to synthesize these extended poly-β-ketone chains have been unsuccessful. Polypyrones, containing potential polyketide chains, appeared to offer a feasible solution. Synthesis of these compounds by fusing successive C₃ units to triacetic lactone proved successful, and by this method, bis-, tris-, and tetrapyrone systems were constructed. Basic hydrolysis of these fused pyrone systems, followed by intramolecular aldol condensation, demonstrated that naturally occurring phenolic compounds could be synthesized by the cyclization of a polyketide intermediate.

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