{"id":{"repo_id":"brock","oai_identifier":"oai:brocku.scholaris.ca:10464/17120"},"canonical_url":"https://search.dev.ndltd.org/etd/brock/oai:brocku.scholaris.ca:10464/17120","repository":{"repo_id":"brock","name":"Brock University","base_url":"https://brocku.scholaris.ca/server/oai/request"},"display":{"title":"Approaches Towards a Total Synthesis of Daphenylline","abstract":"The following work describes the synthesis of advanced intermediates enroute to daphenylline. Construction of the ABCE tetracyclic skeleton of daphenylline was accomplished in thirteen steps with seven percent overall yield from commercially available (S)-carvone through [3,3]-allyl cyanate-to-isocyanate rearrangement, intramolecular Heck Reaction, and Intermolecular Diels-Alder/benzannulation strategies. Efforts towards the synthesis of daphenylline’s D ring are discussed. A terse introduction to the scientific literature of daphniphyllum alkaloids and a comprehensive overview of selected approaches and all previous syntheses of daphenylline is given. Experimental procedures and spectroscopic data are provided for all new compounds.","abstract_html":"The following work describes the synthesis of advanced intermediates enroute to daphenylline. Construction of the ABCE tetracyclic skeleton of daphenylline was accomplished in thirteen steps with seven percent overall yield from commercially available (S)-carvone through [3,3]-allyl cyanate-to-isocyanate rearrangement, intramolecular Heck Reaction, and Intermolecular Diels-Alder/benzannulation strategies. Efforts towards the synthesis of daphenylline’s D ring are discussed. A terse introduction to the scientific literature of daphniphyllum alkaloids and a comprehensive overview of selected approaches and all previous syntheses of daphenylline is given. Experimental procedures and spectroscopic data are provided for all new compounds.","abstract_has_math":false,"creators":["Miskey, Scott"],"institution":"Brock University","degree_name":"M.Sc. Chemistry","degree_level":"Masters","degree_discipline":"Faculty of Mathematics and Science","degree_department":"Department of Chemistry","school":null,"contributors":[],"advisors":[],"committee_chairs":[],"committee_members":[],"year":2022,"date_issued":"2022-12-14T20:41:59Z","date_published":"2022-12-14T20:41:59Z","updated_at":"2026-07-24T01:23:07Z","subjects":["Total Synthesis","Natural Products","Daphenylline","Daphniphyllum Alkaloids","Sigmatropic Rearrangement"],"languages":["eng"],"rights":["Attribution-NonCommercial-NoDerivatives 4.0 International"],"rights_urls":["http://creativecommons.org/licenses/by-nc-nd/4.0/"],"identifier_entries":[]},"links":{"outbound_url":"http://hdl.handle.net/10464/17120","outbound_label":"Handle","outbound_source":"dc:identifier.uri"},"metadata_groups":[{"id":"people","label":"People","entries":[{"key":"dc:contributor.department","label":"Department","values":["Department of Chemistry"]},{"key":"dc:creator","label":"Author","values":["Miskey, Scott"]}]},{"id":"academic_context","label":"Academic Context","entries":[{"key":"dc:date.accessioned","label":"Dc Date Accessioned","values":["2022-12-14T20:41:59Z"]},{"key":"dc:date.available","label":"Dc Date Available","values":["2022-12-14T20:41:59Z"]},{"key":"dc:date.issued","label":"Date","values":["2022-12-14T20:41:59Z"]},{"key":"dc:type","label":"Dc Type","values":["Electronic Thesis or Dissertation"]},{"key":"thesis:degree_discipline","label":"Discipline","values":["Faculty of Mathematics and Science"]},{"key":"thesis:degree_level","label":"Degree Level","values":["Masters"]},{"key":"thesis:degree_name","label":"Degree Name","values":["M.Sc. 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Construction of the ABCE tetracyclic skeleton of daphenylline was accomplished in thirteen steps with seven percent overall yield from commercially available (S)-carvone through [3,3]-allyl cyanate-to-isocyanate rearrangement, intramolecular Heck Reaction, and Intermolecular Diels-Alder/benzannulation strategies. Efforts towards the synthesis of daphenylline’s D ring are discussed. A terse introduction to the scientific literature of daphniphyllum alkaloids and a comprehensive overview of selected approaches and all previous syntheses of daphenylline is given. Experimental procedures and spectroscopic data are provided for all new compounds."]},{"key":"dc:title","label":"Title","values":["Approaches Towards a Total Synthesis of Daphenylline"]}]}],"canonical_facts":{"dc:contributor.department":["Department of Chemistry"],"dc:creator":["Miskey, Scott"],"dc:date.accessioned":["2022-12-14T20:41:59Z"],"dc:date.available":["2022-12-14T20:41:59Z"],"dc:date.issued":["2022-12-14T20:41:59Z"],"dc:description.abstract":["The following work describes the synthesis of advanced intermediates enroute to daphenylline. Construction of the ABCE tetracyclic skeleton of daphenylline was accomplished in thirteen steps with seven percent overall yield from commercially available (S)-carvone through [3,3]-allyl cyanate-to-isocyanate rearrangement, intramolecular Heck Reaction, and Intermolecular Diels-Alder/benzannulation strategies. Efforts towards the synthesis of daphenylline’s D ring are discussed. A terse introduction to the scientific literature of daphniphyllum alkaloids and a comprehensive overview of selected approaches and all previous syntheses of daphenylline is given. Experimental procedures and spectroscopic data are provided for all new compounds."],"dc:identifier.uri":["http://hdl.handle.net/10464/17120"],"dc:language.iso":["eng"],"dc:rights":["Attribution-NonCommercial-NoDerivatives 4.0 International"],"dc:rights.uri":["http://creativecommons.org/licenses/by-nc-nd/4.0/"],"dc:subject":["Total Synthesis","Natural Products","Daphenylline","Daphniphyllum Alkaloids","Sigmatropic Rearrangement"],"dc:title":["Approaches Towards a Total Synthesis of Daphenylline"],"dc:type":["Electronic Thesis or Dissertation"],"thesis:degree_discipline":["Faculty of Mathematics and Science"],"thesis:degree_level":["Masters"],"thesis:degree_name":["M.Sc. Chemistry"],"thesis:institution_name":["Brock University"]},"updated_at":"2026-07-24T01:23:07Z"}