The Enantioselective Synthesis of Eburnamonine, Eucophylline, and 16′‐ <i>epi</i> ‐Leucophyllidine

A synthetic approach to the heterodimeric bisindole alkaloid leucophyllidine is disclosed herein. An enantioenriched lactam building block, synthesized through palladium-catalyzed asymmetric allylic alkylation, served as precursor both hemispheres. The eburnamonine-derived fragment was a Bischler–Napieralski/hydrogenation approach, while eucophylline-derived by Friedländer quinoline synthesis and two sequential C−H functionalization steps. convergent Stille coupling phenol-directed hydrogenation united monomeric fragments afford 16′-epi-leucophyllidine in 21 steps from commercial material.