Total synthesis of (ent)-korupensamine D

The first total synthesis of the enantiomer of the natural product, korupensamine D (16R), is described. The key steps include a highly efficient preparation of the enantiomerically pure primary amine 4 via the ring opening of aziridine 2 with an arylcuprate reagent and the development of a one-pot selective functionalization of a hindered secondary amine in the presence of phenolic hydroxyl groups (i.e. 8 to 9).