Regiodivergent synthesis of trisubstituted furans through Tf(2)O-catalyzed Friedel-Crafts acylation: a tool for access to tetrahydrofuran lignan analogues |
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Authors: | Comegna Daniela DellaGreca Marina Rosaria Iesce M Previtera Lucio Zarrelli Armando Zuppolini Simona |
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Affiliation: | Dipartimento di Chimica Organica e Biochimica, Università Federico II, Complesso Universitario di Monte S. Angelo, via Cinthia 4, I-80126, Naples, Italy. daniela.comegna@unina.it |
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Abstract: | 3- or 4-Aroylfurans have been prepared selectively and in high yields from a common precursor by simple tuning of reaction conditions in Friedel-Crafts acylation promoted by triflic anhydride. The formation of products can be explained on the basis of the ring-chain tautomerism occurring in compounds equipped with two neighbouring carboxylic functions. Since 4-aroylfuran derivatives show a typical lignan backbone, suitable hydrogenation conditions were found out to gain tetrahydrofuran lignans. |
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