H. Maruyama, M. Shiozaki, T. Hiraoka
Nov 1, 1985
Citations
0
Influential Citations
21
Citations
Journal
Bulletin of the Chemical Society of Japan
Abstract
L-Threonine was converted to a versatile azetidinone derivative stereospecifically in 3 steps. This azetidinone was further transformed to (3S,4R)-3-[(R)-1-hydroxyethyl]-1-(4-methoxybenzyl)-4-[(phenylthio)-carbonylmethyl]-2-azetidinone (S-Phenyl thioester), a key intermediate for the synthesis of thienamycin and it’s biologically active analogs. Since the thiol part of this S-phenyl thioester can be exchanged easily with other complex or useful thiols under mild conditions, important S-thioester precursors for the production of carbapenem analogs were obtained in high yield.