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Communication | Regular issue | Vol 41, No. 9, 1995, pp.1891-1900
Published online, 1st January, 1970
DOI: 10.3987/COM-95-7119
The Syntheses of 1α-Fluoro-1β-methylcarbapenem Esters

Kenneth J. Wildonger, William J. Leanza, Ronald W. Ratcliffe, and James P. Springer

*Department of Medicinal Chemistry, Merck Research Laboratories, P.O.Box 2000, Rahway, NJ 07065, U.S.A.


The synthesis of p-nitrobenzyl (1S,3R,5S,6S)-1-fluoro-1-methyl-2-oxo-6-[(1R)-1-[(tert-butyldimethylsilyl)oxyl]ethyl]carbapenam-3-carboxylate and allyl (1R,5S,6S)-6-[(1R)-1-[(allyloxycarbonyloxy)ethyl]-1-fluoro-1-methyl-2-phenylcarbapen-2-em-3-carboxylate is detailed. The difficulties encountered in further chemical elaboration of these analogs are reported.