Enantiomerically Pure b-Lactams with the Thienamycin Side Chain via Glycosylation

Easy access to both enantiomers of blactarns with the thienamycin side chain was achieved via iodine catalyzed Ferrier reaction with commercially available tri-0-acetyl-D-glucal.A new chapter in p-lactam chemistry was initiated in 1976 with the discovery of the p-lactam antibiotic thienamycin2 (la) with a carbon side chain in place of an amide side chain that characterizes penicillins and cephalosporins.This is also the first p-lactam antibiotic in clinical use to be manufactured by total synthesis3 rather than by fermentation.Other antibiotics of the thienamycin type include PS-5 (lh), carpetimycin (lc) and many synthetic carbapenems.Analogs of 1 are still being prepared by medicinal chemists.