Jozimine B, a Constitutionally Unsymmetric, Antiplasmodial ‘Dimer’ of the Naphthylisoquinoline Alkaloid Ancistrocladine

The first synthesis of a constitutionally unsymmetric bis-naphthylisoquinoline, the unnatural ‘dimer’ of the Ancistrocladus alkaloid ancistrocladine, jozimine B, is described. The constitution and the configuration at the new, central biaryl axis were established through extensive NMR investigations and quantum chemical CD calculations. Compared with ancistrocladine, its only weakly antiplasmodial monomeric precursor, jozimine B exhibits a distinctly enhanced antimalarial activity.