A highly efficient synthesis of lamellarins K and L by the Michael addition/ring-closure reaction of benzyldihydroisoquinoline derivatives with ethoxycarbonyl-β-nitrostyrenes

Abstract

Alkaloid achievement: Lamellarins, a new class of potential nontoxic inhibitors of HIV-1 integrase that are also responsible for multidrug-resistance reversal in cancer cell lines, could be synthesized in three chemical steps and in 60% overall yields from two simple starting materials (see scheme). The key step in the convergent synthetic approach involved the novel Michael addition/ring-closure reaction to give the pyrrole core and the ester group required for subsequent lactonization in one step.