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.
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.
Beauhaire
Josiane
J
Unité de Phytopharmacie et Médiateurs Chimiques, Inra, Route de Saint-Cyr, 78026 Versailles Cedex, France.
Es-Safi
Nour-Eddine
NE
Boyer
François-Didier
FD
Kerhoas
Lucien
L
Guernevé
Christine le
Cl
Ducrot
Paul-Henri
PH
D000975:Antioxidants / Q000138:chemical synthesis; D044946:Biflavonoids / Q000737:chemistry; D002392:Catechin / Q000737:chemistry; D019281:Dimerization; D004986:Ether / Q000737:chemistry; D044945:Proanthocyanidins / Q000138:chemical synthesis* / Q000737:chemistry
D000975:Antioxidants; D044946:Biflavonoids; D044945:Proanthocyanidins; D004986:Ether; C013221:proanthocyanidin; C017674:procyanidin; D002392:Catechin