Molecular complexity from aromatics: Synthesis and photoreaction of endo-tricyclo[5.2.2.02,6]undecane—A stereoselective route to tricyclic framework of protoilludanes

A stereoselective route towards protoilludanoids from simple aromatic precursor is described. The methodology involves in situ generation of spiroepoxycyclohexadienone and cycloaddition with cyclopentadiene and photochemical 1,3-acyl shift.