Recherche de nouveaux antiviraux phosphoniques : utilisation du fluorure de potassium sur alumine pour la fonctionnalisation de méthylènes activés et préparation d'analogues de nucléotides

Abstract : Aiming at the preparation of new phosphonic anti-viral compounds, tetraethyl methylenediphosphonate was functionallized using KF-alumina as a solid base. Synthetic methods were designed for the preparation of phosphonic S,S-acetals, phosphonic S,S-ketene acetals, branched cyclopropanylidene- diphosphonates and diazophosphonates. Phosphonic S,S-ketene acetals were transformed into phosphonic ketene acetals, into phosphonic N,N-ketene acetals and into gemdialkylethenediylidenediphosphonates. A new method was designed for the synthesis of alpha-ketodithioesters from methylketones via pyridinium salts. We studied the condensation of benzaldehyde with methylenediphosphonate in the presence of solid catalysts, and the Wittig-Horner reaction was the only one observed. A new sulfur analog of 9-(2-(phosphonomethoxy)-ethyl)adenine was prepared.
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Frederic Thibault-Starzyk. Recherche de nouveaux antiviraux phosphoniques : utilisation du fluorure de potassium sur alumine pour la fonctionnalisation de méthylènes activés et préparation d'analogues de nucléotides. Chimie organique. Université de Caen, 1992. Français. ⟨tel-02172404⟩

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