The Absolute Configuration of Michellamine B, a “Dimeric”, Anti‐HIV‐Active Naphthylisoquinoline Alkaloid

Ruthenium-mediated oxidative degradation led to the elucidation of the absolute configuration of michellamine B (1), the most active representative of a new class of naturally occurring “dimeric” naphthylisoquinolinealkaloids. Based on the degradation products, D-alanine and the (R)-3-aminobutyric acid, and the fact that the relative configurations of the stereocenters and the axis within the two molecular “halves” is known, 1 is deduced to have a (1 R,3R,5M,1‴ R,3‴ R,5‴ P) configuration.