Different approaches to the asymmetric synthesis of 1,3,6-trisubstituted and 1,2,3,6-tetrasubstituted carbapenems from D-glucosamine

Article abstract of DOI:10.1016/0957-4166(95)00045-Q

Different stereocontrolled syntheses of optically active 1,3,6-trisubstituted and 1,2,3,6-tetrasubstituted carbapenems are reported. D-glucosamine, as chiral auxiliary, trans-cinnamaldehyde and methoxyacetyl chloride were used as starting materials in the Staudinger ketene-imine monobactam formation. Radical cyclization and oxidation reactions led to the desired carbapenems.