{"id":{"repo_id":"uiuc","oai_identifier":"oai:www.ideals.illinois.edu:2142/84220"},"canonical_url":"https://search.dev.ndltd.org/etd/uiuc/oai:www.ideals.illinois.edu:2142/84220","repository":{"repo_id":"uiuc","name":"University of Illinois - Urbana-Champaign","base_url":"https://www.ideals.illinois.edu/oai-pmh"},"display":{"title":"The Asymmetric Total Synthesis of Cephalotaxine","abstract":"A unique method for the formation of [3]benzazepines, via the [3,3]-sigmatropic rearrangement of 1-vinyl-2-aryl-aziridines, has been developed and applied to the synthesis of the Cephalotaxus alkaloids. The synthetic approach begins with D-ribose and utilizes the [3,3] sigmatropic rearrangement of a highly functionalized 1-vinyl-2-aryl aziridine and a diastereoselective intermolecular [3+2] cycloaddition of a non-stabilized azomethine ylide as the key steps. This work has resulted in an asymmetric total synthesis of cephalotaxine in 24 steps and 0.9% overall yield.","abstract_html":"A unique method for the formation of [3]benzazepines, via the [3,3]-sigmatropic rearrangement of 1-vinyl-2-aryl-aziridines, has been developed and applied to the synthesis of the Cephalotaxus alkaloids. The synthetic approach begins with D-ribose and utilizes the [3,3] sigmatropic rearrangement of a highly functionalized 1-vinyl-2-aryl aziridine and a diastereoselective intermolecular [3+2] cycloaddition of a non-stabilized azomethine ylide as the key steps. This work has resulted in an asymmetric total synthesis of cephalotaxine in 24 steps and 0.9% overall yield.","abstract_has_math":false,"creators":["Eckelbarger, Joseph David"],"institution":"University of Illinois at Urbana-Champaign","degree_name":"Ph.D.","degree_level":"Dissertation","degree_discipline":"Chemistry","degree_department":null,"school":null,"contributors":["Gin, David Y."],"advisors":[],"committee_chairs":[],"committee_members":[],"year":2015,"date_issued":"2015-09-25T22:13:32Z","date_published":"2015-09-25T22:13:32Z","updated_at":"2026-07-22T22:26:22Z","subjects":["Chemistry, Organic"],"languages":["eng"],"rights":[],"rights_urls":[],"identifier_entries":[{"key":"dc:identifier","label":"Identifier","values":["(MiAaPQ)AAI3223583"],"render_values":[{"text":"(MiAaPQ)AAI3223583","href":null,"code":true}]}]},"links":{"outbound_url":"http://hdl.handle.net/2142/84220","outbound_label":"Handle","outbound_source":"dc:identifier"},"metadata_groups":[{"id":"people","label":"People","entries":[{"key":"dc:contributor","label":"Contributor","values":["Gin, David Y."]},{"key":"dc:creator","label":"Author","values":["Eckelbarger, Joseph David"]}]},{"id":"academic_context","label":"Academic Context","entries":[{"key":"dc:date","label":"Dc Date","values":["2015-09-25T22:13:32Z","10000-01-01","2006"]},{"key":"dc:type","label":"Dc Type","values":["text"]},{"key":"thesis:degree_discipline","label":"Discipline","values":["Chemistry"]},{"key":"thesis:degree_level","label":"Degree Level","values":["Dissertation"]},{"key":"thesis:degree_name","label":"Degree Name","values":["Ph.D."]},{"key":"thesis:institution_name","label":"Thesis Institution Name","values":["University of Illinois at Urbana-Champaign"]}]},{"id":"subjects_keywords","label":"Subjects and Keywords","entries":[{"key":"dc:subject","label":"Dc Subject","values":["Chemistry, Organic"]}]},{"id":"language_rights","label":"Language and Rights","entries":[{"key":"dc:language","label":"Dc Language","values":["eng"]}]},{"id":"identifiers","label":"Identifiers","entries":[{"key":"dc:identifier","label":"Identifier","values":["http://hdl.handle.net/2142/84220","(MiAaPQ)AAI3223583"]}]},{"id":"additional","label":"Additional Metadata","entries":[{"key":"dc:description","label":"Description","values":["A unique method for the formation of [3]benzazepines, via the [3,3]-sigmatropic rearrangement of 1-vinyl-2-aryl-aziridines, has been developed and applied to the synthesis of the Cephalotaxus alkaloids. 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