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Fenestradiènes et cyclooctatriènes : synthèse directe par réaction en cascade palladocatalysée

Abstract : This PhD thesis focuses on the study of methodologies employing cascade reactions and allowed access to a large variety of highly tense and functionalized polycyclic structures as fenestradienes and cyclooctatrienes. Those cascades reactions are initiated by a 4-exo-dig cyclocarbopalladation followed by a Sonogashira cross-coupling. Under appropriate conditions, an alkyne addition reaction on a triple bond allow to access a tetraene intermediate, Those four conjugated double bonds realize a conrotatory Sn electrocyclization. Under microwave irradiation conditions control, a supplementary 6n lectrocyclization can be performed. Several examples of [4.6.4.6] fenestradienes, 6-4-8 and 7-4-8 cyclooctatrienes have been synthesized, employing the same starting material and widely used catalysts and reactants. A particular attention is paid to alkyne addition reaction, which is carried out in the studied palladocatalyzed cascade reaction.
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Mélanie Charpenay. Fenestradiènes et cyclooctatriènes : synthèse directe par réaction en cascade palladocatalysée. Autre. Université de Strasbourg, 2012. Français. ⟨NNT : 2012STRAF040⟩. ⟨tel-00836869⟩

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