Synthesis of highly functionalized tropolones by rhodium(II)-catalyzed reactions of vinyldiazomethanes with oxygenated dienes

Article abstract of DOI:10.1016/S0040-4020(01)89604-6

Rhodium(II) catalyzed decomposition of vinyldiazomethanes to vinylcarbenoids in the presence of oxygenated dienes leads to the regioselective synthesis of cycloheptadienes by a tandem cyclopropanation/Cope rearrangement. The resulting cycloheptadienes are readily hydrolyzed and oxidized, leading to a very direct and general synthesis of highly functionalized tropolones.