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Vers la synthèse totale de la Lannotinidine A

Abstract : The scope of the modified Julia olefination has previously been broadened to various carboxylic acid derivatives in our laboratory, and more particularly to imides in an intramolecular fashion. This methodology allows us access to bicyclic quinolizidines bearing an enamide or vinylsulfone moiety. We chose to use this key intermediate in the total synthesis of the Lannotinidine A, a Lycopodium alkaloid isolated in 2005. The natural product has never been synthesized before, and this thesis describes various synthetics approaches studied in order to obtain it. Examination of each disconnection revealed new reactivities of the enamide functional group and highlighted the importance of the rings system in the different transformations. Thorough study of each disconnection unlocked a synthetic pathway toward the natural product using the Diels-Alder reaction on an innovative substrate. Thanks to this key reaction, various tetracyclic analogues of Lannotinidine A were synthesized, and the different stereoisomers identified. The synthesis of a library of analogues of the natural product also allowed for stereoselectivity rationalization on each step, depending on the diastereoisomer used.
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Submitted on : Wednesday, June 22, 2022 - 3:15:14 PM
Last modification on : Thursday, August 4, 2022 - 5:14:34 PM


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  • HAL Id : tel-03701886, version 1


Bastien Raison. Vers la synthèse totale de la Lannotinidine A. Chimie organique. Université de Lyon, 2021. Français. ⟨NNT : 2021LYSE1271⟩. ⟨tel-03701886⟩



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