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.*.
","abstract_html":"<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>","abstract_has_math":false,"creators":["Lin, Weimin"],"institution":null,"degree_name":"Doctor of Philosophy","degree_level":"Dissertation","degree_discipline":null,"degree_department":null,"school":null,"contributors":["Charles K Zercher"],"advisors":[],"committee_chairs":[],"committee_members":[],"year":2006,"date_issued":"2006-01-01T08:00:00Z","date_published":"2006-01-01T08:00:00Z","updated_at":"2026-07-24T05:22:19Z","subjects":["Chemistry","Organic"],"languages":[],"rights":[],"rights_urls":[],"identifier_entries":[]},"links":{"outbound_url":"https://scholars.unh.edu/dissertation/344","outbound_label":"Repository record","outbound_source":"dc:identifier"},"metadata_groups":[{"id":"people","label":"People","entries":[{"key":"dc:contributor","label":"Contributor","values":["Charles K Zercher"]},{"key":"dc:creator","label":"Author","values":["Lin, Weimin"]}]},{"id":"academic_context","label":"Academic Context","entries":[{"key":"thesis:degree_level","label":"Degree Level","values":["Dissertation"]},{"key":"thesis:degree_name","label":"Degree Name","values":["Doctor of Philosophy"]}]},{"id":"subjects_keywords","label":"Subjects and Keywords","entries":[{"key":"dc:subject","label":"Dc Subject","values":["Chemistry","Organic"]}]},{"id":"identifiers","label":"Identifiers","entries":[{"key":"dc:identifier","label":"Identifier","values":["https://scholars.unh.edu/dissertation/344"]}]},{"id":"additional","label":"Additional Metadata","entries":[{"key":"dc:description.abstract","label":"Abstract","values":["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.*.
"]},{"key":"dc:title","label":"Title","values":["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"]}]}],"canonical_facts":{"dc:contributor":["Charles K Zercher"],"dc:creator":["Lin, Weimin"],"dc:description.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.*.
"],"dc:identifier":["https://scholars.unh.edu/dissertation/344"],"dc:subject":["Chemistry","Organic"],"dc:title":["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"],"thesis:degree_level":["Dissertation"],"thesis:degree_name":["Doctor of Philosophy"]},"updated_at":"2026-07-24T05:22:19Z"}