Spiroaminal model systems of the marineosins with final step pyrrole incorporation

In this Letter, we describe a short, six step enantioselective route to spiroaminal lactam model systems reminiscent of marineosins A and B that has been developed starting from either (R)- or (S)-hydroxysuccinic acid, respectively, in ∼9% overall yield. This route enables late stage incorporation of the pyrrole ring at C5 via nucleophilic displacement of an iminium triflate salt.