Diels-Alder cycloaddition of o-quinonedimethides and alkylidene-5H-furan-2-ones: new and rapid access to lambertellol cores and arthrinone derivatives

An efficient synthesis of deoxy-lambertellols was reported through a highly chemo-and diastereoselective intermolecular Diels-Alder cycloaddition between trans-1,2-disiloxybenzocyclobutenes and 2-methylprotoanemonine. Such transformation with delta-substituted gamma-alkylidenebutenolides, to prepare new analogues of these tricyclic spirolactones, which would be very difficult to prepare by other ways, was also studied.