3-(2-Alkoxy-1-hydroxyethyl)azetidin-2-ones: Potential Intermediates for the Synthesis of Novel Carbapenems

Abstract

3-Vinyl and 3-isopropenylazetidin-2-ones can be transformed into the corresponding 3-(2-alkoxy-1-hydroxyethyl)azetidin-2-ones and 3-(1-alkoxy-2-hydroxypropan-2-yl)azetidin-2-ones by regioselective alcoholysis of 3-(1,2-epoxyethyl)azetidin-2-ones; 4-acetoxy-3-(1-hydroxy-2-methoxyethyl)-1-(4-methoxyphenyl)azetidin-2-one 14 is a synthetic precursor for carbapenems having both alcohol and alkoxyalcohol substituents at C-8.