Asymmetric Total Syntheses of Naphthylisoquinoline Alkaloids via Atroposelective Coupling Reaction Using Central Chirality as Atroposelectivity-Controlling Group.

Abstract

We describe the asymmetric total syntheses of naphthylisoquinoline alkaloids. Atroposelective biaryl coupling reaction between naphthyl pinacol boronate and an aryl iodide, bearing (S)-2-aminopropyl group at the ortho-position using the existing central chirality as an atroposelectivity-controlling group, provided the desired biaryl product with high atroposelectivity, without the use of an external chiral source. From the resulting biaryl product, several naphthylisoquinoline alkaloids were prepared via the stereoselective formation of the isoquinoline framework with the appropriate oxidation state and stereochemistry.