A chiral synthesis of trans-carbapenam-3-carboxylic acid and the assignment of (3S,5S) configuration to the corresponding product from Serratia and Erwinia species

Abstract

A convenient stereoselective synthesis of (3R,5R)-carbapenam-3-carboxylic acid from D-(R)-glutamic acid is described and the product shown to be enantiomeric with that isolated from Serratia and Erwinia species; this represents the first naturally occurring carbapenem or carbapenam with (5S) ring junction geometry to be reported.