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Stereoselective Synthesis of 2-Aryltetrahydrofuran-3,4-dicarboxylate Derivatives: Efficient Approach to Tetrahydrofuran Lignans
31 December 2000 (online)
A convenient and stereoselective synthetic route to the precursor of natural products, lignans, containing tetrahydrofuran has been developed. A series of asymmetric 2-aryltetrahydrofuran-3,4-carboxylic acid derivatives were synthesized in high yields with this route. The effect of substituents on the Diels-Alder reaction of aryl-substituted oxazoles with alkyne dienophile and on the catalytic hydrogenation of dimethyl 2-arylfuran-3,4-dicarboxylates has been investigated. The regioselective hydrolyses of the dimethyl ester group was also studied. All products were characterized by elemental analysis, FT-IR, 1H NMR and MS.
stereoselectivity - Diels-Alder reactions - hydrogenation - hydrolysis - furans