Total synthesis of (+)-okaramine J featuring an exceptionally facile N-reverse-prenyl to C-prenyl Aza-Claisen rearrangement

Abstract

The convergent total synthesis of (+)-okaramine J was achieved in a longest linear sequence of 12 steps from L-tryptophan tert-butyl ester. A key reaction was the acid-catalyzed room-temperature aza-Claisen rearrangement of a N-reverse-prenylated hexahydro[2,3-b]pyrroloindole to a C-prenylated derivative