The Application of Gold(I)-Catalysed Intramolecular Hydroarylation Reactions to the Synthesis of Coumarins

Abstract

The studies disclosed in the body of this thesis were focused on the preparation of coumarin derivatives from aryl propiolates using gold(I)-catalysed intramolecular hydroarylation reactions (IMHA). Chapter One focuses on the currently available synthetic methods for the preparation of coumarins. Chapter Two begins with a discussion of the mechanism of the IMHA process by which the author has prepared coumarins from aryl propiolates. Then, it focuses on the implementation of the IMHA reaction in the synthesis of coumarins (C, X=O) from aryl propiolates (B) that are themselves derived from the corresponding phenol (A). The extension of such procedures to related system, chromene (X=Me2), is also described. Chapter Three focuses on the application of the new methodology to natural product synthesis, particularly, fraxetin and some of its derivatives as well as pimpinellin.