The development of the zinc-mediated tandem chain extension-acylation reaction for the synthesis of spiro-fused ketals was successfully accomplished. The incorporation of a methyl-substituent into the gamma-keto ester backbone, through a methyl substituted carbenoid, allowed for the synthesis of papyracillic acid B and 4-epi-papyracillic acid C. Comparison between the reported and experimental spectral data for papyracillic acid B and 4- epi-papyracillic acid C permitted structural and stereochemical reassignment.
Diastereoselective syntheses of beta-methyl-gamma-keto esters were achieved through the utility of an L-serine auxiliary. Preparation of a series of L-serine derived precursors were prepared and studied.
","abstract_html":"<p>The development of the zinc-mediated tandem chain extension-acylation reaction for the synthesis of spiro-fused ketals was successfully accomplished. The incorporation of a methyl-substituent into the gamma-keto ester backbone, through a methyl substituted carbenoid, allowed for the synthesis of papyracillic acid B and 4-epi-papyracillic acid C. Comparison between the reported and experimental spectral data for papyracillic acid B and 4- epi-papyracillic acid C permitted structural and stereochemical reassignment.</p><p>Diastereoselective syntheses of beta-methyl-gamma-keto esters were achieved through the utility of an L-serine auxiliary. Preparation of a series of L-serine derived precursors were prepared and studied.</p>","abstract_has_math":false,"creators":["Mazzone, Jennifer R"],"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":2011,"date_issued":"2011-01-01T08:00:00Z","date_published":"2011-01-01T08:00:00Z","updated_at":"2026-07-24T05:22:36Z","subjects":["Chemistry","Organic"],"languages":[],"rights":[],"rights_urls":[],"identifier_entries":[]},"links":{"outbound_url":"https://scholars.unh.edu/dissertation/644","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":["Mazzone, Jennifer R"]}]},{"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/644"]}]},{"id":"additional","label":"Additional Metadata","entries":[{"key":"dc:description.abstract","label":"Abstract","values":["The development of the zinc-mediated tandem chain extension-acylation reaction for the synthesis of spiro-fused ketals was successfully accomplished. The incorporation of a methyl-substituent into the gamma-keto ester backbone, through a methyl substituted carbenoid, allowed for the synthesis of papyracillic acid B and 4-epi-papyracillic acid C. Comparison between the reported and experimental spectral data for papyracillic acid B and 4- epi-papyracillic acid C permitted structural and stereochemical reassignment.
Diastereoselective syntheses of beta-methyl-gamma-keto esters were achieved through the utility of an L-serine auxiliary. Preparation of a series of L-serine derived precursors were prepared and studied.
"]},{"key":"dc:title","label":"Title","values":["I The synthesis of papyracillic acids: Application of the tandem chain extension-acylation reaction II Diastereoselective synthesis of beta-methyl-gamma-keto esters through the utility of an L-serine auxiliary"]}]}],"canonical_facts":{"dc:contributor":["Charles K Zercher"],"dc:creator":["Mazzone, Jennifer R"],"dc:description.abstract":["The development of the zinc-mediated tandem chain extension-acylation reaction for the synthesis of spiro-fused ketals was successfully accomplished. The incorporation of a methyl-substituent into the gamma-keto ester backbone, through a methyl substituted carbenoid, allowed for the synthesis of papyracillic acid B and 4-epi-papyracillic acid C. Comparison between the reported and experimental spectral data for papyracillic acid B and 4- epi-papyracillic acid C permitted structural and stereochemical reassignment.
Diastereoselective syntheses of beta-methyl-gamma-keto esters were achieved through the utility of an L-serine auxiliary. Preparation of a series of L-serine derived precursors were prepared and studied.
"],"dc:identifier":["https://scholars.unh.edu/dissertation/644"],"dc:subject":["Chemistry","Organic"],"dc:title":["I The synthesis of papyracillic acids: Application of the tandem chain extension-acylation reaction II Diastereoselective synthesis of beta-methyl-gamma-keto esters through the utility of an L-serine auxiliary"],"thesis:degree_level":["Dissertation"],"thesis:degree_name":["Doctor of Philosophy"]},"updated_at":"2026-07-24T05:22:36Z"}