Synthetic studies of carbapenem and penem antibiotics. I. Facile synthesis of a key intermediate: 4-Acetoxy-3-(1-hydroxyethyl)-2-azetidinone

Article abstract of DOI:10.1248/cpb.39.1931

A highly efficient synthesis of (3R,4R)-4-acetoxy-3-[(R)-1-hydroxyethyl]-2-azetidinone, which is a key intermediate for the synthesis of carbapenem and penem antibiotics, was accomplished. It was found that oxymercuration-reduction of easily obtainable 4-alkyloxycarbonyl-1-(di-p-anisylmethyl)-3-ethenyl-2-azetidinone could be employed as a key stereoselective reaction. The chiral starting material was obtained by optical resolution or asymmetric (2 + 2) cycloaddition. The desired product was afforded in four steps, that is, oxymercuration-reduction, oxidative decarboxylation, protection of the hydroxy group and removal of the N-protecting group.

Full text of DOI:10.1248/cpb.39.1931

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