Diels-Alder cycloaddition of o-quinonedimethides and alkylidene-5H-furan-2-ones: new and rapid access to lambertellol cores and arthrinone derivatives |
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Authors: | Blanc Romain Héran Virginie Rahmani Raphaël Commeiras Laurent Parrain Jean-Luc |
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Institution: | Aix-Marseille Université, Institut des Sciences Moléculaires de Marseille, iSm2-UMR CNRS 6263, Centre Saint Jér?me, Service 532, 13397 Marseille Cedex 20, France. |
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Abstract: | 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 δ-substituted γ-alkylidenebutenolides, to prepare new analogues of these tricyclic spirolactones, which would be very difficult to prepare by other ways, was also studied. |
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