Convergent syntheses of oral THF 1beta-methylcarbapenems.
Convergent syntheses of oral THF 1beta-methylcarbapenems 4 (OCA-983) and 5 starting from M2-phosphate 1 were developed. Reaction of the M2-phosphate 1 with THF thiols containing a requisite prodrug side chain, 9 and 10, gave the desired oral THF 1beta-methylcarbapenems 4 and 5, respectively, in 46% and 42% overall yields.
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Chemical Sciences, Wyeth-Ayerst Research, Pearl River, NY 10965, USA.
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Lin
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D000818:Animals; D001419:Bacteria / Q000187:drug effects; D015780:Carbapenems / Q000096:biosynthesis* / Q000494:pharmacology / Q000627:therapeutic use; D004927:Escherichia coli Infections / Q000188:drug therapy; D009682:Magnetic Resonance Spectroscopy; D051379:Mice; D008826:Microbial Sensitivity Tests; D016339:Spectrometry, Mass, Fast Atom Bombardment; D013203:Staphylococcal Infections / Q000188:drug therapy
D015780:Carbapenems