Stereoselective Synthesis of 2-Aryltetrahydrofuran-3,4-dicarboxylate Derivatives: Efficient Approach to Tetrahydrofuran Lignans

Abstract

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, 1 H NMR and MS.

Regiodivergent synthesis of trisubstituted furans through Tf2O-catalyzed Friedel–Crafts acylation: a tool for access to tetrahydrofuranlignan analogues

“…To test this synthetic opportunity, model furan 3a was hydrogenated at high pressure (100 atm) with Pd on carbon, as already reported for 2-arylfuran-3,4-dicarboxylate esters, 22 under different temperature conditions.…”

Isocyanide‐based three‐component synthesis of functionalized 5‐alkylimino‐2,5‐dihydrofuran‐3,4‐dicarboxylate and their conversion to substituted furanones

“…In conclusion, a facile one‐pot method for the synthesis of 5‐alkylimino‐2,5‐dihydrofuran‐3,4‐dicarboxylate derivatives from readily accessible precursors has been proceed. These compounds are important starting materials in the synthesis of natural products containing tetrahydrofuran rings [10]. Hydrolysis of these compounds with HCl (5%) produced furanones in dichloromethane as the solvent.…”

“…Furthermore, polyfunctionalized furans are versatile synthetic starting materials for the preparation of a variety of heterocyclic and acyclic compounds [1–9]. Especially, 2,5‐disubstituted furan‐3,4‐dicarboxylates are very important starting materials in the synthesis of natural products containing tetrahydrofuran rings [10]. So far, many synthetic protocols for the synthesis of iminolactones have been reported.…”

Reaction between cyclohexy isocyanide, dialkyl acetylenedicarboxylates and 1-aryl-2-ene-3-acetyl-1,4-diketones. One-pot synthesis of highly functionalized 5-cyclohexylimino-2,5-dihydrofurans

“…10-17 2,5-Disubstituted dihydrofuran-3,4-dicarboxylates are important starting materials which have been used for the synthesis of some natural products. 18 Thus, developing new, simple and efficient syntheses of dihydrofuran derivatives have been an area of interest.…”