Regiospecific synthesis of polysubstituted furans from silylated furans: Expedient syntheses of rosefuran

Article abstract of DOI:10.1016/S0040-4020(97)00083-5

By utilizing a sequence of regiospecific lithiation-alkylation, ipso-iodination, boroxine formation, Sonogashira cross-coupling, nickel-catalyzed cross-coupling and Suzuki cross-coupling reactions, several methods have been developed for the syntheses of 2,3-disubstituted furans; 2,4-disubstituted furans, 2,3,4-trisubstituted furans and 2,3,5-trisubstituted furans; Our approach uses as the key theme trimethylsilyl groups as both blacking groups as well as ipso-directing groups. The advantage of this program is aptly illustrated by two expedient syntheses of rosefuran (9c).