{"id":{"repo_id":"aachen","oai_identifier":"oai:publications.rwth-aachen.de:62267"},"canonical_url":"https://search.dev.ndltd.org/etd/aachen/oai:publications.rwth-aachen.de:62267","repository":{"repo_id":"aachen","name":"RWTH Aachen University","base_url":"https://publications.rwth-aachen.de/oai2d"},"display":{"title":"Asymmetrische Synthese von Dibenzylbutan- und Dibenzylbutyrolacton-Lignanen","abstract":"Lignans are a wide spread class of natural compounds which mainly occur in plants as secondary plant metabolites. The term lignans is derived from Latin lignum (wood). Lignans are still very interesting and intensively investigated mostly due to their great variety of medical important bioactivities (antitumor-, antimitotic- and antiviral properties) which they possess. For the organic chemist, the stereochemical structure and the variety of lignans subclasses are the most interesting challenge. This thesis describes the application of a chiral a-aminonitrile in the Michael addition to cyclic and open-chained Michael acceptors. The emphasis of this work is the synthesis of lignans. Different lignans like dibenzylbutan lignan from Virola sebifera, (+)-hinokinin, (+)-dihydrocubebin and cubebindimethylether were synthesised with high diastereo- and enantiomeric excesses. Furthermore, chiral a-aminonitrile were also used in the intramolecular Michael addition to achieve the synthesis of 4-chromanones as well of isopilocarpine.","abstract_html":"Lignans are a wide spread class of natural compounds which mainly occur in plants as secondary plant metabolites. The term lignans is derived from Latin lignum (wood). Lignans are still very interesting and intensively investigated mostly due to their great variety of medical important bioactivities (antitumor-, antimitotic- and antiviral properties) which they possess. For the organic chemist, the stereochemical structure and the variety of lignans subclasses are the most interesting challenge. This thesis describes the application of a chiral a-aminonitrile in the Michael addition to cyclic and open-chained Michael acceptors. The emphasis of this work is the synthesis of lignans. Different lignans like dibenzylbutan lignan from Virola sebifera, (+)-hinokinin, (+)-dihydrocubebin and cubebindimethylether were synthesised with high diastereo- and enantiomeric excesses. 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