The underutilized intramolecular arene/allene cycloaddition described decades ago by Himbert permits rapid access to strained polycyclic compounds. Metathesis rearrangement of the cycloadducts yields functional-group-rich polycycles of potential utility for natural product synthesis and medicinal chemistry. Advantages of the developed method include a simple approach to the starting materials and in situ generation of allenes. The topologically complex products resemble the Erythrina family of alkaloids which exhibit interesting neurobiological activities. Thus, our products may provide useful lead compounds in this area.

Generating complexity in two steps via benzene Diels–Alder reaction and rearrangement metathesis

245th National Meeting (2013)

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