Stereoselective synthesis of 2-aryltetrahydrofuran-3,4-dicarboxylate derivatives: Efficient approach to tetrahydrofuran lignans

A convenient and stereoselective synthetic route to the precursor of natura l products, lignans, containing tetrahydrofuran has been developed. A serie s of asymmetric 2-aryltetrahydrofuran-3,4-carboxylic acid derivatives were synthesized in high yields with this route. The effect of substituents on t he Diels-Alder reaction of aryl-substituted oxazoles with alkyne dienophile and on the catalytic hydrogenation of dimethyl 2-arylfuran-3, 4-dicarboxyl ates has been investigated. The regioselective hydrolyses of the dimethyl e ster group was also studied. All products were characterized by elemental a nalysis, FT-IR,H-1 NMR and MS.