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Synthesis 2000; 2000(14): 2069-2077
DOI: 10.1055/s-2000-8725
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Stereoselective Synthesis of 2-Aryltetrahydrofuran-3,4-dicarboxylate Derivatives: Efficient Approach to Tetrahydrofuran Lignans

Weiwei Pei* , Jian Pei, Shaohui Li, Xiulin Ye
  • *Department of Chemistry, Peking University, Beijing 100871, People's Republic of China; Fax +6 58 72 75 28; E-mail: j-pei@imre.org.sg
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Publication Date:
31 December 2000 (online)

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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