Date of Award
Fall 2006
Project Type
Dissertation
Program or Major
Chemistry
Degree Name
Doctor of Philosophy
First Advisor
Charles K Zercher
Abstract
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.*.
Recommended Citation
Lin, Weimin, "I Peptide isosteric replacement preparation using zinc-mediated chain extension-aldol reactions II Formal synthesis of (+)-Brefeldin A III Zinc-mediated chain extension reactions with substituted carbenoids" (2006). Doctoral Dissertations. 344.
https://scholars.unh.edu/dissertation/344