The formal synthesis of lucentamycin A: Construction of cis-2,3-disubstituted pyrrolidine core by application of SmI2-DMPU system

The formal synthesis of lucentamycin A (1) was accomplished in 14 steps from D-serine methyl ester as a starting material. All the requisite stereogenic centers on the pyrrolidine core of 1 were controlled by SmI2-mediated cyclization. Construction of the methyl unit at the C9 position of 1 was achieved by decarbonylation of lactol 11 with stoichiometric amount of Rh(PPh3)(3)Cl. (C) 2018 Elsevier Ltd. All rights reserved.