Synthesis of modified proanthocyanidins: easy and general introduction of a hydroxy group at C-6 of catechin; efficient synthesis of elephantorrhizol.
A general procedure for the oxidation of catechin derivatives is described, leading to the introduction of a new hydroxy group at C-6. This procedure has been applied for the synthesis of elephantorrhizol, a natural flavan-3-ol exhibiting a fully substituted cycle A.
Boyer
François-Didier
FD
Unité de Phytopharmacie et Médiateurs Chimiques, Inra, Route de Saint-Cyr, 78026 Versailles Cedex, France.
Es-Safi
Nour-Eddine
NE
Beauhaire
Josiane
J
Guernevé
Christine Le
CL
Ducrot
Paul-Henri
PH
D000975:Antioxidants / Q000138:chemical synthesis; D002392:Catechin / Q000737:chemistry; D005419:Flavonoids / Q000138:chemical synthesis*; D015394:Molecular Structure; D010946:Plants, Medicinal / Q000737:chemistry; D044945:Proanthocyanidins / Q000138:chemical synthesis*
D000975:Antioxidants; D005419:Flavonoids; D044945:Proanthocyanidins; C500877:elephantorrhizol; C013221:proanthocyanidin; C404987:flavan-3-ol; D002392:Catechin