Synthetic studies of proanthocyanidins. Highly stereoselective synthesis of the catechin dimer, procyanidin-B3.
A stereoselective synthesis of benzylated procyanidin-B3, a condensed catechin dimer, is described. Condensation of 5,7,3',4'-tetrabenzylcatechin with (2R,3S,4S)-5,7,3',4'-tetrabenzyloxy-3-acetoxy-4-methoxyflavan as an electrophile in the presence of TiCl4 led to octabenzylated procyanidin-B3 stereoselectively.
D000872:Anthocyanins / Q000138:chemical synthesis*; D044946:Biflavonoids; D002392:Catechin; D002625:Chemistry, Organic / Q000379:methods; D019906:Nuclear Magnetic Resonance, Biomolecular; D009904:Optical Rotation; D044945:Proanthocyanidins
D000872:Anthocyanins; D044946:Biflavonoids; D044945:Proanthocyanidins; C427205:proanthocyanidin B3; C479581:procyanidin B3; D002392:Catechin