A facile and efficacious route to the benzooxabicyclo [3.2. 1] octane system has been developed and applied to a synthesis of filiformin (1). The cycloaddition of ethylene to the methoxychromone 13 furnished the oxetanol 14 through a tandem cycloaddition and γ- hydrogen abstraction sequence. Lithium aluminum hydride reduction to the diol 15 followed by acid-catalyzed rearrangement produced benzooxabicyclooctanone (16), arising from ...
