{"id":{"repo_id":"aachen","oai_identifier":"oai:publications.rwth-aachen.de:61685"},"canonical_url":"https://search.dev.ndltd.org/etd/aachen/oai:publications.rwth-aachen.de:61685","repository":{"repo_id":"aachen","name":"RWTH Aachen University","base_url":"https://publications.rwth-aachen.de/oai2d"},"display":{"title":"Asymmetrische Synthese von 3-Oxa-15-Deoxy-16-(m-tolyl)-Tetranorisocarbacyclin und 15-Deoxy-16-(m-tolyl)-Tetranorisocarbacyclin","abstract":"Some years ago besides the known prostacyclin receptor (IP1) a new prostacyclin-specific receptor (IP2) was discovered in the brains of different mammals. Both receptors show different binding-affinities towards stable prostacyclin-analogues. Prostacyclin-analogue 15-deoxy-16-(m-tolyl)-17,18,19,20-tetranorisocarbacyclin (15-deoxy-TIC) binds with high affinity and selectivity to the IP2-receptor. 15-deoxy-TIC prevents neuronal death in vitro and in vivo and can pass the blood-brain-barrier. Because of these properties 15-deoxy-TIC can possibly be used as a drug against Alzheimers and Parkinsons diseases. This thesis describes the asymmetric total synthesis of the new prostacyclin-analogue 3-oxa-15-deoxy-TIC and a formal total synthesis of the known 15-deoxy-TIC. It is to be expected that under physiological conditions 3-oxa-15-deoxy-TIC is metabolically more stable than 15-deoxy-TIC. The key steps in the syntheses of the target molecules are a conjugate addition of a copperorganyl to an azoalkene and an asymmetric Horner-Wadsworth-Emmons reaction using a chiral phosphonate.","abstract_html":"Some years ago besides the known prostacyclin receptor (IP1) a new prostacyclin-specific receptor (IP2) was discovered in the brains of different mammals. Both receptors show different binding-affinities towards stable prostacyclin-analogues. Prostacyclin-analogue 15-deoxy-16-(m-tolyl)-17,18,19,20-tetranorisocarbacyclin (15-deoxy-TIC) binds with high affinity and selectivity to the IP2-receptor. 15-deoxy-TIC prevents neuronal death in vitro and in vivo and can pass the blood-brain-barrier. Because of these properties 15-deoxy-TIC can possibly be used as a drug against Alzheimers and Parkinsons diseases. This thesis describes the asymmetric total synthesis of the new prostacyclin-analogue 3-oxa-15-deoxy-TIC and a formal total synthesis of the known 15-deoxy-TIC. It is to be expected that under physiological conditions 3-oxa-15-deoxy-TIC is metabolically more stable than 15-deoxy-TIC. The key steps in the syntheses of the target molecules are a conjugate addition of a copperorganyl to an azoalkene and an asymmetric Horner-Wadsworth-Emmons reaction using a chiral phosphonate.","abstract_has_math":false,"creators":["van de Sande, Marc"],"institution":"Mainz","degree_name":null,"degree_level":null,"degree_discipline":null,"degree_department":null,"school":null,"contributors":["Gais, Hans-Joachim"],"advisors":[],"committee_chairs":[],"committee_members":[],"year":2007,"date_issued":"2007","date_published":"2007","updated_at":"2026-07-30T19:43:10Z","subjects":["info:eu-repo/classification/ddc/540","Chemie","Asymmetrische Synthese","Isocarbacyclin","Prostacyclinanaloga","15-Deoxy-TIC","Medizinische Chemie","Prostacyclin-Rezeptor","asymmetric synthesis","medicinal chemistry","prostacyclin receptor"],"languages":["ger"],"rights":["info:eu-repo/semantics/openAccess"],"rights_urls":[],"identifier_entries":[{"key":"dc:identifier","label":"Identifier","values":["https://publications.rwth-aachen.de/search?p=id:%22RWTH-CONV-123321%22"],"render_values":[{"text":"https://publications.rwth-aachen.de/search?p=id:%22RWTH-CONV-123321%22","href":"https://publications.rwth-aachen.de/search?p=id:%22RWTH-CONV-123321%22","code":true}]}]},"links":{"outbound_url":"https://publications.rwth-aachen.de/record/61685","outbound_label":"Repository record","outbound_source":"dc:identifier"},"metadata_groups":[{"id":"people","label":"People","entries":[{"key":"dc:contributor","label":"Contributor","values":["Gais, Hans-Joachim"]},{"key":"dc:creator","label":"Author","values":["van de Sande, Marc"]}]},{"id":"academic_context","label":"Academic Context","entries":[{"key":"dc:coverage","label":"Dc Coverage","values":["DE"]},{"key":"dc:date","label":"Dc Date","values":["2007"]},{"key":"dc:publisher","label":"Institution","values":["Mainz"]},{"key":"dc:relation","label":"Dc Relation","values":["info:eu-repo/semantics/altIdentifier/urn/urn:nbn:de:hbz:82-opus-18157"]},{"key":"dc:type","label":"Dc Type","values":["info:eu-repo/semantics/doctoralThesis","info:eu-repo/semantics/publishedVersion"]}]},{"id":"subjects_keywords","label":"Subjects and Keywords","entries":[{"key":"dc:subject","label":"Dc Subject","values":["info:eu-repo/classification/ddc/540","Chemie","Asymmetrische Synthese","Isocarbacyclin","Prostacyclinanaloga","15-Deoxy-TIC","Medizinische Chemie","Prostacyclin-Rezeptor","asymmetric synthesis","medicinal chemistry","prostacyclin receptor"]}]},{"id":"language_rights","label":"Language and Rights","entries":[{"key":"dc:language","label":"Dc Language","values":["ger"]},{"key":"dc:rights","label":"Dc Rights","values":["info:eu-repo/semantics/openAccess"]}]},{"id":"identifiers","label":"Identifiers","entries":[{"key":"dc:identifier","label":"Identifier","values":["https://publications.rwth-aachen.de/record/61685","https://publications.rwth-aachen.de/search?p=id:%22RWTH-CONV-123321%22"]}]},{"id":"additional","label":"Additional Metadata","entries":[{"key":"dc:description","label":"Description","values":["Some years ago besides the known prostacyclin receptor (IP1) a new prostacyclin-specific receptor (IP2) was discovered in the brains of different mammals. Both receptors show different binding-affinities towards stable prostacyclin-analogues. Prostacyclin-analogue 15-deoxy-16-(m-tolyl)-17,18,19,20-tetranorisocarbacyclin (15-deoxy-TIC) binds with high affinity and selectivity to the IP2-receptor. 15-deoxy-TIC prevents neuronal death in vitro and in vivo and can pass the blood-brain-barrier. Because of these properties 15-deoxy-TIC can possibly be used as a drug against Alzheimers and Parkinsons diseases. This thesis describes the asymmetric total synthesis of the new prostacyclin-analogue 3-oxa-15-deoxy-TIC and a formal total synthesis of the known 15-deoxy-TIC. It is to be expected that under physiological conditions 3-oxa-15-deoxy-TIC is metabolically more stable than 15-deoxy-TIC. The key steps in the syntheses of the target molecules are a conjugate addition of a copperorganyl to an azoalkene and an asymmetric Horner-Wadsworth-Emmons reaction using a chiral phosphonate."]},{"key":"dc:source","label":"Dc Source","values":["Aachen : Mainz, Aachener Beiträge zur Chemie 73, VIII, 139 S. (2007). = Zugl.: Aachen, Techn. Hochsch., Diss., 2006"]},{"key":"dc:title","label":"Title","values":["Asymmetrische Synthese von 3-Oxa-15-Deoxy-16-(m-tolyl)-Tetranorisocarbacyclin und 15-Deoxy-16-(m-tolyl)-Tetranorisocarbacyclin"]}]}],"canonical_facts":{"dc:contributor":["Gais, Hans-Joachim"],"dc:coverage":["DE"],"dc:creator":["van de Sande, Marc"],"dc:date":["2007"],"dc:description":["Some years ago besides the known prostacyclin receptor (IP1) a new prostacyclin-specific receptor (IP2) was discovered in the brains of different mammals. Both receptors show different binding-affinities towards stable prostacyclin-analogues. Prostacyclin-analogue 15-deoxy-16-(m-tolyl)-17,18,19,20-tetranorisocarbacyclin (15-deoxy-TIC) binds with high affinity and selectivity to the IP2-receptor. 15-deoxy-TIC prevents neuronal death in vitro and in vivo and can pass the blood-brain-barrier. Because of these properties 15-deoxy-TIC can possibly be used as a drug against Alzheimers and Parkinsons diseases. This thesis describes the asymmetric total synthesis of the new prostacyclin-analogue 3-oxa-15-deoxy-TIC and a formal total synthesis of the known 15-deoxy-TIC. It is to be expected that under physiological conditions 3-oxa-15-deoxy-TIC is metabolically more stable than 15-deoxy-TIC. The key steps in the syntheses of the target molecules are a conjugate addition of a copperorganyl to an azoalkene and an asymmetric Horner-Wadsworth-Emmons reaction using a chiral phosphonate."],"dc:identifier":["https://publications.rwth-aachen.de/record/61685","https://publications.rwth-aachen.de/search?p=id:%22RWTH-CONV-123321%22"],"dc:language":["ger"],"dc:publisher":["Mainz"],"dc:relation":["info:eu-repo/semantics/altIdentifier/urn/urn:nbn:de:hbz:82-opus-18157"],"dc:rights":["info:eu-repo/semantics/openAccess"],"dc:source":["Aachen : Mainz, Aachener Beiträge zur Chemie 73, VIII, 139 S. (2007). = Zugl.: Aachen, Techn. 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