Exploratory studies toward a total synthesis of pericine (subincanadine E)

A possible synthetic approach to the bridged indole alkaloid pericine (subincanadine E), based on the combination of a ring-closing metathesis (RCM) and a Heck cyclization, is described. After having developed a convenient RCM-based route to tricyclic intermediates embodying the central nine-membered ring, the closure of the strained 1-azabicyclo[5.2.2]undecane framework of the alkaloid using a vinyl halide Heck coupling was pursued without success.