Biomimetic Synthesis of the Antimalarial Flindersial Alkaloids

A biomimetic strategy for the synthesis of the antimalarial flindersial alkaloids is described. Flinderoles A, B, and C, desmethylflinderole C, isoborreverine, and dimethylisoborreverine were all synthesized in three steps from tryptamine. The key step is an acid-promoted dimerization of the natural product borrerine. This approach is thought to mirror the biosynthesis of these compounds.