{"id":{"repo_id":"uiuc","oai_identifier":"oai:www.ideals.illinois.edu:2142/84270"},"canonical_url":"https://search.dev.ndltd.org/etd/uiuc/oai:www.ideals.illinois.edu:2142/84270","repository":{"repo_id":"uiuc","name":"University of Illinois - Urbana-Champaign","base_url":"https://www.ideals.illinois.edu/oai-pmh"},"display":{"title":"Development of a Diastereoselective [4+2]-Annulation of Vinyl Carbodiimides With Chiral N-Alkyl Imines and Its Application to the Synthesis of the Batzelladine Alkaloids: Total Synthesis of (+)-Batzelladine a and (-)-Batzelladine D","abstract":"A diastereoselective [4+2] annulation of vinyl carbodiimides with chiral N-alkyl imines has been developed to access the stereochemically rich anti-fused polycyclic guanidine cores of the batzelladine alkaloids. Application of this strategy, together with additional key steps such as a long-range directed hydrogenation and a diastereoselective intramolecular iodoamination, led to highly convergent total syntheses of (-)-batzelladine D and (+)-batzelladine A with excellent stereocontrol. Overall, a 13 step asymmetric synthesis of -(-)batzelladine D was accomplished in 7.4% yield, and a 20 step asymmetric synthesis of (+)-batzelladine A was completed in 2.0% yield. Investigations into the application of the imine/vinyl carbodiimide [4+2]-annulation to the syn-fused tricyclic guanidine cores of the batzelladines are also described.","abstract_html":"A diastereoselective [4+2] annulation of vinyl carbodiimides with chiral N-alkyl imines has been developed to access the stereochemically rich anti-fused polycyclic guanidine cores of the batzelladine alkaloids. Application of this strategy, together with additional key steps such as a long-range directed hydrogenation and a diastereoselective intramolecular iodoamination, led to highly convergent total syntheses of (-)-batzelladine D and (+)-batzelladine A with excellent stereocontrol. Overall, a 13 step asymmetric synthesis of -(-)batzelladine D was accomplished in 7.4% yield, and a 20 step asymmetric synthesis of (+)-batzelladine A was completed in 2.0% yield. Investigations into the application of the imine/vinyl carbodiimide [4+2]-annulation to the syn-fused tricyclic guanidine cores of the batzelladines are also described.","abstract_has_math":false,"creators":["Arnold, Michael A."],"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":"2015-09-25T22:13:44Z","date_published":"2015-09-25T22:13:44Z","updated_at":"2026-07-22T22:26:22Z","subjects":["Chemistry, Organic"],"languages":["eng"],"rights":[],"rights_urls":[],"identifier_entries":[{"key":"dc:identifier","label":"Identifier","values":["(MiAaPQ)AAI3290168"],"render_values":[{"text":"(MiAaPQ)AAI3290168","href":null,"code":true}]}]},"links":{"outbound_url":"http://hdl.handle.net/2142/84270","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":["Arnold, Michael A."]}]},{"id":"academic_context","label":"Academic Context","entries":[{"key":"dc:date","label":"Dc Date","values":["2015-09-25T22:13:44Z","10000-01-01","2007"]},{"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/2142/84270","(MiAaPQ)AAI3290168"]}]},{"id":"additional","label":"Additional Metadata","entries":[{"key":"dc:description","label":"Description","values":["A diastereoselective [4+2] annulation of vinyl carbodiimides with chiral N-alkyl imines has been developed to access the stereochemically rich anti-fused polycyclic guanidine cores of the batzelladine alkaloids. Application of this strategy, together with additional key steps such as a long-range directed hydrogenation and a diastereoselective intramolecular iodoamination, led to highly convergent total syntheses of (-)-batzelladine D and (+)-batzelladine A with excellent stereocontrol. Overall, a 13 step asymmetric synthesis of -(-)batzelladine D was accomplished in 7.4% yield, and a 20 step asymmetric synthesis of (+)-batzelladine A was completed in 2.0% yield. Investigations into the application of the imine/vinyl carbodiimide [4+2]-annulation to the syn-fused tricyclic guanidine cores of the batzelladines are also described.","Made available in DSpace on 2015-09-25T22:13:44Z (GMT). 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Application of this strategy, together with additional key steps such as a long-range directed hydrogenation and a diastereoselective intramolecular iodoamination, led to highly convergent total syntheses of (-)-batzelladine D and (+)-batzelladine A with excellent stereocontrol. Overall, a 13 step asymmetric synthesis of -(-)batzelladine D was accomplished in 7.4% yield, and a 20 step asymmetric synthesis of (+)-batzelladine A was completed in 2.0% yield. Investigations into the application of the imine/vinyl carbodiimide [4+2]-annulation to the syn-fused tricyclic guanidine cores of the batzelladines are also described.","Made available in DSpace on 2015-09-25T22:13:44Z (GMT). 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