FROM PENICILLIN TO PENEM AND CARBAPENEM. II. SYNTHESIS OF 3,4-DISUBSTITUTED AZETIDINONE DERIVATIVES FROM 6,6-BIS(PHENYLSELENYL)PENICILLANATE

Article abstract of DOI:10.1016/S0040-4039(00)88685-2

6,6-Bis(phenylselenyl)penicillanate 2a was converted into 6-1'-(R)-hydroxyethyl substituted penicillanate 5 in high yield.Compound 5 was deselenylated to 10.Oxidation, and then the basic epimerization of cis sulfone 11 gave trans sulfone derivative 12.The trans sulfone 12 was degraded to the monocyclic β-lactams 14, 15 which are important precursors for the carbapenem synthesis.