Total Synthesis of (±)-Sceptrin

Organic Letters 22(17), 6698-6702, DOI: 10.1021/acs.orglett.0c01381

A four-step synthesis of the dimeric pyrrole–imidazole alkaloid sceptrin is reported. The brevity of the route is based on a simple solution developed for selective assembly of the cyclobutane core of the natural product. The photochemical intermolecular [2 + 2] dimerization of a useful hymenidin surrogate enables direct entry to this enigmatic class of biologically active marine secondary metabolites.