<br/>The C1 substituent of the carbapenems has proven useful in protecting this class of antibiotic from human renal dehydropeptidase I, thus prolonging half-life, and for improving activity against selected pathogens. In order to facilitate scaleup and handling, we desired to develop a method to incorporate selected C1 substituents which did not involve the use of organometallics, strong bases (e.g. LDA), or chiral auxiliaries. We will discuss zinc chloride promoted reactions of silyl enol ethers with 4-acetoxyazetidinones with respect to stereoselectivity and ability to incoporate various substituents at the C1 position of the carbapenems.

Approaches to the synthesis of C1-substituted carbapenems

249th National Meeting (2015)

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