Exploratory studies toward a total synthesis of the marine ascidian metabolite perophoramidine

A strategy for a total synthesis of the marine alkaloid perophoramidine has been investigated. Key steps which have been tested include a tandem intramolecular Heck/carbonylation reaction and a stereoselective allylation of a pentacyclic δ-lactam to produce the C-4/20 vicinal quaternary centers having the requisite relative configuration of the metabolite.