Date of Award

Fall 2006

Project Type


Program or Major


Degree Name

Doctor of Philosophy

First Advisor

Charles K Zercher


A series of amino acid derived alpha-substituted-gamma-keto amides and esters have been prepared by zinc-mediated chain extension and tandem chain extension aldol reactions with various aldehydes and ketones. An efficient diastereoselective synthetic route has been developed to approach a proposed inhibitor for HCMV (Human Cytomegalovirus) protease using this zinc-mediated tandem chain extension-aldol reaction as the key step. An asymmetric formal synthesis of (+)-Brefeldin A has been developed in which the zinc-mediated ring expansion/oxidation/elimination method constitutes a key step. Preparation of beta-alkyl-gamma-keto esters through a chain extension reaction using substituted carbenoids has also been accomplished.*.