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- W2534709957 abstract "The thesis describes the first total synthesis of Eucophylline, the south fragment of the Leucophyllidine alkaloid recently isolated from Leuconotis griffithiiand L. eugenifolius. The 10-step synthesis encompasses a new straight forward method to access to the azabicyclo[3.3.1]nonane skeleton through a free-radical three-component olefinic carbo-oximation process. During these studies, we also isolated enamines exhibiting unusual stabilities resulting from their strained bicyclicconformation. The synthesis of the Eburnane part, the north fragment of Leucophyllidine, was developed relying on a new free-radical three-component Carbo-Cyanation reaction. This new reaction showed high tolerance toward different functional groups and provided an efficient mean to install the nitrile group in complex structures and to introduce quaternary centers. The biomimetic coupling between the Eburnane and Eucophylline fragments was finally studied using structurally similar models. Preliminary results of this model study showed that absence of a gemdimethyleffect in the Eburnane model probably prevents the formation of the cyclicimine, key intermediate for the desired coupling." @default.
- W2534709957 created "2016-10-28" @default.
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- W2534709957 date "2016-09-23" @default.
- W2534709957 modified "2023-09-27" @default.
- W2534709957 title "Total synthesis of eucophylline : a free-radical approach towards total synthesis of cytotoxic leucophyllidine" @default.
- W2534709957 hasPublicationYear "2016" @default.
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