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Synthèse de dérivés de l'acide tétronique et de l'acide pulvinique. Synthèse totale de la norbadione A.

Abstract : Many pigments of fungi, such as norbadione A and pulvinic acid derivatives, revealed remarkable antioxidant activity. In this thesis, we were interested in the synthesis of these compounds, which could be used as agents for protection against ionizing radiations. In this context, a new synthetic pathway to tetronic acid derivatives has been developed from methyl arylacetates and hydroxyesters. The methodology allowed one-step synthesis of several 3-aryltetronic acids and related heterocyclic compounds. From one tetronic acid derivative, three natural pulvinic acid esters have been prepared, by a very direct way and with very good yields. In the total synthesis of norbadione A, two pathways have been studied. The first one relied on the methodology developed in this thesis for the synthesis of pulvinic acids. The preparation of an advanced intermediate was obtained. The second pathway, in which the key step was a double Suzuki-Miyaura cross-coupling, led to the first total synthesis of norbadione A.
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Aurélie Mallinger. Synthèse de dérivés de l'acide tétronique et de l'acide pulvinique. Synthèse totale de la norbadione A.. Sciences du Vivant [q-bio]. Université Paris Sud - Paris XI, 2008. Français. ⟨tel-00553463⟩

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