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

<p>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.*.</p>

Name thesis:degree_name

Doctor of Philosophy

Level thesis:degree_level

Dissertation

Year

2006

Author dc:creator

• Lin, Weimin

Contributors dc:contributor

• Charles K Zercher

• Chemistry
• Organic

Repository record dc:identifier

https://scholars.unh.edu/dissertation/344

OAI identifier oai:identifier

oai:scholars.unh.edu:dissertation-1343