Stereoselective total synthesis of amicoumacin C

The enantio- and diastereoselective total synthesis of amicoumacin C was achieved from l-phenylalanine in 17% overall yield through 13 steps via condensation between an amine and an acid segment. The amine segment was prepared from l-leucine in 42% yield by a 7-step sequence involving a diastereoselective reduction of an α-dibenzylamino ketone intermediate, while the acid segment was obtained from l-phenylalanine by using acidic hydrolysis of an acetonide-protected amide accompanied by concomitant lactonization as a key step.