Synthesis of modified proanthocyanidins: introduction of acyl substituents at C-8 of catechin. Selective synthesis of a C-4-->O-->C-3 ether-linked procyanidin-like dimer |
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Authors: | Beauhaire Josiane Es-Safi Nour-Eddine Boyer François-Didier Kerhoas Lucien Guernevé Christine le Ducrot Paul-Henri |
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Institution: | Unité de Phytopharmacie et Médiateurs Chimiques, Inra, Route de Saint-Cyr, 78026 Versailles Cedex, France. |
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Abstract: | The regioselective introduction of substituents at C-8 of (+)-catechin is described, leading to the synthesis of several catechin derivatives with various substitution patterns to be used for the further synthesis of modified proanthocyanidins. Thereafter, a new 3-O-4 ether-linked procyanidin-like derivative was synthesized. Its formation was selectively achieved through TiCl(4)-catalyzed condensation of 4-(2-hydroxyethoxy)tetra-O-benzyl catechin with the 8-trifluoroacetyl adduct of tetra-O-benzyl catechin. |
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