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.
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