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Etude de nouvelles réactions radicalaires. Application à la synthèse de composés polycycliques.

Abstract : This thesis highlights, through two examples, the potential of the radical chemistry of xanthates to achieve radical reactions normally considered difficult. After a brief introduction on chain propagation radical chemistry and more specifically the radical chemistry of xanthates, a new methodology for the synthesis of spirocyclic compounds, and in particular gamma-spirolactones, is presented. It centres around a dearomatising spirocyclisation onto a furan moiety and can be extended to the synthesis of spirolactames by replacing the furan ring with a pyrrole. In a second part, a new approach towards the synthesis of analogs of Colchicine, a molecule isolated from Colchicum autumnale which is well known for its anticancer properties, is described. It relies upon the formation of the 7-membered B ring of this molecule in 2 or 3 steps using radical chemistry giving a quick access to a variety of analogs.
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Submitted on : Thursday, July 29, 2010 - 1:47:27 PM
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  • HAL Id : pastel-00002173, version 1



Soizic Guindeuil. Etude de nouvelles réactions radicalaires. Application à la synthèse de composés polycycliques.. Chimie organique. Ecole Polytechnique X, 2006. Français. ⟨pastel-00002173⟩



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