{"id":{"repo_id":"bayreuth","oai_identifier":"oai:epub.uni-bayreuth.de:919"},"canonical_url":"https://search.dev.ndltd.org/etd/bayreuth/oai:epub.uni-bayreuth.de:919","repository":{"repo_id":"bayreuth","name":"Universität Bayreuth","base_url":"https://epub.uni-bayreuth.de/cgi/oai2"},"display":{"title":"Keteneylidenetriphenylphosphorane as a 'C2O building block' in the synthesis of highly functionalised tetramic and tetronic acids","abstract":"Naturally occurring 4-hydroxy-pyrrol-2(5H)-ones and 4-hydroxy-furan-2(5H)-ones are known to possess a wide range of biological activities such as anti-viral and tumour inhibition. For this reason, the synthesis of a number of these compounds was attempted, namely Tenuazonic Acid, Reutericyclin and Carlosic acid. A general synthesis of 4-hydroxy-pyrrol-2-ones was established by reaction of a phosphorus ylide (Ph3PCCO) with a variety of amino esters. A number of derivatives were prepared with varying substituents at the 3- and 5-positions of the nitrogen heterocycle. A general method for the preparation of highly functionalised furan-2-ones from simple alpha-hydroxy esters was also developed. Progress has been made in the synthesis of N-substituted pyrrol-2-ones where simple amide esters were reacted with a phosphorus ylide (Ph3PCCO) in the construction of highly functionalised nitrogen heterocycles. A new acylation procedure was developed in order to selectively introduce an acetyl residue to pyrrolidine-2-ones and furan-2-ones. A phosphorus ylide (Ph3PCCO) and its solid supported variant were used as acylating agents under relatively mild, basic conditions. Complex heterocycles were prepared using the Diels-Alder methodology and from reaction of Ph3PCCO with relatively simple molecules.","abstract_html":"Naturally occurring 4-hydroxy-pyrrol-2(5H)-ones and 4-hydroxy-furan-2(5H)-ones are known to possess a wide range of biological activities such as anti-viral and tumour inhibition. For this reason, the synthesis of a number of these compounds was attempted, namely Tenuazonic Acid, Reutericyclin and Carlosic acid. A general synthesis of 4-hydroxy-pyrrol-2-ones was established by reaction of a phosphorus ylide (Ph3PCCO) with a variety of amino esters. A number of derivatives were prepared with varying substituents at the 3- and 5-positions of the nitrogen heterocycle. A general method for the preparation of highly functionalised furan-2-ones from simple alpha-hydroxy esters was also developed. Progress has been made in the synthesis of N-substituted pyrrol-2-ones where simple amide esters were reacted with a phosphorus ylide (Ph3PCCO) in the construction of highly functionalised nitrogen heterocycles. A new acylation procedure was developed in order to selectively introduce an acetyl residue to pyrrolidine-2-ones and furan-2-ones. A phosphorus ylide (Ph3PCCO) and its solid supported variant were used as acylating agents under relatively mild, basic conditions. Complex heterocycles were prepared using the Diels-Alder methodology and from reaction of Ph3PCCO with relatively simple molecules.","abstract_has_math":false,"creators":["Melanophy, Claire"],"institution":"Universität Bayreuth","degree_name":null,"degree_level":"thesis.doctoral","degree_discipline":null,"degree_department":null,"school":null,"contributors":["Schobert, Rainer"],"advisors":[],"committee_chairs":[],"committee_members":[],"year":2004,"date_issued":"2004-07-22","date_published":"2004-07-22","updated_at":"2026-07-27T18:49:29Z","subjects":[],"languages":[],"rights":[],"rights_urls":[],"identifier_entries":[]},"links":{"outbound_url":"https://epub.uni-bayreuth.de/id/eprint/919/","outbound_label":"Repository record","outbound_source":"source_url"},"metadata_groups":[{"id":"people","label":"People","entries":[{"key":"dc:contributor","label":"Contributor","values":["Schobert, Rainer"]},{"key":"dc:creator","label":"Author","values":["Melanophy, Claire"]}]},{"id":"academic_context","label":"Academic Context","entries":[{"key":"dc:publisher","label":"Institution","values":["Universität Bayreuth"]},{"key":"dc:type","label":"Dc Type","values":["doctoralThesis"]},{"key":"thesis:degree_level","label":"Degree Level","values":["thesis.doctoral"]},{"key":"thesis:institution_name","label":"Thesis Institution Name","values":["Universität Bayreuth"]}]},{"id":"additional","label":"Additional Metadata","entries":[{"key":"dc:description.abstract","label":"Abstract","values":["Naturally occurring 4-hydroxy-pyrrol-2(5H)-ones and 4-hydroxy-furan-2(5H)-ones are known to possess a wide range of biological activities such as anti-viral and tumour inhibition. For this reason, the synthesis of a number of these compounds was attempted, namely Tenuazonic Acid, Reutericyclin and Carlosic acid. A general synthesis of 4-hydroxy-pyrrol-2-ones was established by reaction of a phosphorus ylide (Ph3PCCO) with a variety of amino esters. A number of derivatives were prepared with varying substituents at the 3- and 5-positions of the nitrogen heterocycle. A general method for the preparation of highly functionalised furan-2-ones from simple alpha-hydroxy esters was also developed. Progress has been made in the synthesis of N-substituted pyrrol-2-ones where simple amide esters were reacted with a phosphorus ylide (Ph3PCCO) in the construction of highly functionalised nitrogen heterocycles. A new acylation procedure was developed in order to selectively introduce an acetyl residue to pyrrolidine-2-ones and furan-2-ones. A phosphorus ylide (Ph3PCCO) and its solid supported variant were used as acylating agents under relatively mild, basic conditions. Complex heterocycles were prepared using the Diels-Alder methodology and from reaction of Ph3PCCO with relatively simple molecules.","Natürlich vorkommende 4-Hydroxy-pyrrol-2(5H)-one und 4-Hydroxy-furan-2(5H)-one besitzen hohe biologische Aktivität. So zeigen sie unter Anderem anti-virale als auch anti-tumour Eigenschaften. Auf Grund dessen wurde versucht einen synthetischen Zugang zu Tenuazonsäure, Reutericyclin und Carlosischer Säure, zu finden. Ein allgemeiner Syntheseweg zur Herstellung von 4-Hydroxy-pyrrol-2-onen wurde durch die Reaktion von Phosphor Ylid Ph3PCCO mit verschiedenen Aminosäureestern etabliert. Durch die Einführung von verschiedenen Substituenten der 3- und 5-Positionen des Stickstoff-Heterocyclus wurde eine Vielzahl von Derivaten synthetisiert. Zusätzlich wurde auch eine allgemeine Syntheseroute zur Herstelllung von hochfunktionalisierten Furan-2-onen ausgehend von Alpha-Hydroxyestern. Deutliche Fortschritte in Bezug auf die Synthese von N-substituierten Pyrrol-2-onen wurden verzeichnet. Durch Umsatz von einfachen Alpha-Amidoestern mit Phosphor Ylid Ph3PCCO wurden hochfunktionalisierten wurden Stickstoff-Heterocyclen erhalten. Ein neuen Acylierungsmethode zur selektiven Einführung von einem Acetylrest in Pyrrol-2-one und Furan-2-one konnte gefunden und etabliert werden. Phosphor Ylid (Ph3PCCO) und dessen festphasengebundene Variante wurden als Acylierungmittel verwendet. Diese Reaktion wurde unter milden und basischen Bedingungen durchgeführt. Komplexe Heterocycle wurden mittels der Diels-Alder Methode als auch der Reaktion von Ph3PCCO mit relativ einfachen Molekülen hergestellt."]},{"key":"dc:format.medium","label":"Dc Format Medium","values":["application/pdf"]},{"key":"dc:title","label":"Title","values":["Keteneylidenetriphenylphosphorane as a 'C2O building block' in the synthesis of highly functionalised tetramic and tetronic acids"]}]}],"canonical_facts":{"dc:contributor":["Schobert, Rainer"],"dc:creator":["Melanophy, Claire"],"dc:description.abstract":["Naturally occurring 4-hydroxy-pyrrol-2(5H)-ones and 4-hydroxy-furan-2(5H)-ones are known to possess a wide range of biological activities such as anti-viral and tumour inhibition. For this reason, the synthesis of a number of these compounds was attempted, namely Tenuazonic Acid, Reutericyclin and Carlosic acid. A general synthesis of 4-hydroxy-pyrrol-2-ones was established by reaction of a phosphorus ylide (Ph3PCCO) with a variety of amino esters. A number of derivatives were prepared with varying substituents at the 3- and 5-positions of the nitrogen heterocycle. A general method for the preparation of highly functionalised furan-2-ones from simple alpha-hydroxy esters was also developed. Progress has been made in the synthesis of N-substituted pyrrol-2-ones where simple amide esters were reacted with a phosphorus ylide (Ph3PCCO) in the construction of highly functionalised nitrogen heterocycles. A new acylation procedure was developed in order to selectively introduce an acetyl residue to pyrrolidine-2-ones and furan-2-ones. A phosphorus ylide (Ph3PCCO) and its solid supported variant were used as acylating agents under relatively mild, basic conditions. Complex heterocycles were prepared using the Diels-Alder methodology and from reaction of Ph3PCCO with relatively simple molecules.","Natürlich vorkommende 4-Hydroxy-pyrrol-2(5H)-one und 4-Hydroxy-furan-2(5H)-one besitzen hohe biologische Aktivität. So zeigen sie unter Anderem anti-virale als auch anti-tumour Eigenschaften. Auf Grund dessen wurde versucht einen synthetischen Zugang zu Tenuazonsäure, Reutericyclin und Carlosischer Säure, zu finden. Ein allgemeiner Syntheseweg zur Herstellung von 4-Hydroxy-pyrrol-2-onen wurde durch die Reaktion von Phosphor Ylid Ph3PCCO mit verschiedenen Aminosäureestern etabliert. Durch die Einführung von verschiedenen Substituenten der 3- und 5-Positionen des Stickstoff-Heterocyclus wurde eine Vielzahl von Derivaten synthetisiert. Zusätzlich wurde auch eine allgemeine Syntheseroute zur Herstelllung von hochfunktionalisierten Furan-2-onen ausgehend von Alpha-Hydroxyestern. Deutliche Fortschritte in Bezug auf die Synthese von N-substituierten Pyrrol-2-onen wurden verzeichnet. Durch Umsatz von einfachen Alpha-Amidoestern mit Phosphor Ylid Ph3PCCO wurden hochfunktionalisierten wurden Stickstoff-Heterocyclen erhalten. Ein neuen Acylierungsmethode zur selektiven Einführung von einem Acetylrest in Pyrrol-2-one und Furan-2-one konnte gefunden und etabliert werden. Phosphor Ylid (Ph3PCCO) und dessen festphasengebundene Variante wurden als Acylierungmittel verwendet. Diese Reaktion wurde unter milden und basischen Bedingungen durchgeführt. Komplexe Heterocycle wurden mittels der Diels-Alder Methode als auch der Reaktion von Ph3PCCO mit relativ einfachen Molekülen hergestellt."],"dc:format.medium":["application/pdf"],"dc:publisher":["Universität Bayreuth"],"dc:title":["Keteneylidenetriphenylphosphorane as a 'C2O building block' in the synthesis of highly functionalised tetramic and tetronic acids"],"dc:type":["doctoralThesis"],"thesis:degree_level":["thesis.doctoral"],"thesis:institution_name":["Universität Bayreuth"]},"updated_at":"2026-07-27T18:49:29Z"}