The Catalytic Intramolecular Friedel-Crafts Acylation of Meldrum’s Acid Derivatives and The Total Synthesis of Taiwaniaquinol B

Description

A thesis presented to the University of Waterloo in fulfillment of the thesis requirement for the degree of Doctor of Philosophy in Chemistry. – Waterloo, Ontario, Canada, 2005. – 207 p. One of the major goals of modern synthetic organic chemical research is to provide new methodology and reagents that facilitate the synthesis of highly complex carbon-containing molecules, particularly those that might have biological activity or can be incorporated into materials with unique behaviour. The invention of new routes to access small molecule substrates for synthesis, and perhaps as targets themselves, is required to satisfy demands for high yields and to maximize molecular diversity. The ability to manipulate or modify substrates containing a variety of functional groups can simplify a synthetic sequence and improve overall product yields. This thesis describes research into the catalytic formation of benzocyclic ketones. Benzocyclic ketones comprise 1-indanones, 1-tetralones, 1-benzosuberones, and related compoundsIntroduction and Background The Catalytic Intramolecular Friedel-Crafts Acylation of Meldrum’s Acid Derivatives Investigations Into the Mechanism of the Intramolecular Friedel-Crafts Acylation of Meldrum’s Acid Derivatives The Total Synthesis of (±)-Taiwaniaquinol B