title: Regiodivergent synthesis of trisubstituted furans through Tf(2)O-catalyzed Friedel-Crafts acylation: a tool for access to tetrahydrofuran lignan analogues.
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.
authors.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
authors.forename: Daniela
authors.initials: D
authors.lastname: Comegna
authors.forename: Marina
authors.initials: M
authors.lastname: DellaGreca
authors.forename: M
authors.initials: M
authors.lastname: Rosaria Iesce
authors.forename: Lucio
authors.initials: L
authors.lastname: Previtera
authors.forename: Armando
authors.initials: A
authors.lastname: Zarrelli
authors.forename: Simona
authors.initials: S
authors.lastname: Zuppolini
mesh_terms: D000215:Acylation; D002384:Catalysis; D005663:Furans / Q000138:chemical synthesis* / Q000737:chemistry; D017705:Lignans / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism; D013451:Sulfonic Acids / Q000737:chemistry*
chemical_list: D005663:Furans; D017705:Lignans; D013451:Sulfonic Acids; C572228:trifluoromethylsulfonic anhydride