A 1β-methylcarbapenem key intermediate is synthesized from methyl (R)-3-hydroxybutyrate via the diastereoselective alkylation and regioselective cuprate ring opening of a chiral epoxide which is readily prepared from Sharpless asymmetric epoxidation of the corresponding allylic alcohol.
C. Oh and W. Ham, Chem. Commun., 1999, 2365 DOI: 10.1039/A907922J
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