A Rh(II)-catalyzed cycloaddition approach toward the synthesis of komaroviquinone

Using a rhodium(II)-catalyzed cyclization/cycloaddition sequence as the key reaction step, the icetexane core of komaroviquinone was constructed by an intramolecular dipolar-cycloaddition of a carbonyl ylide dipole across a tethered π-bond. The ylide was arrived at by cyclization of a rhodium carbenoid intermediate onto a proximal ester group. Efforts toward the preparation of the required precursor for elaboration to the natural product are discussed.