Stereospecific synthesis and antibiotic activity of some cephalosporin analogs

Abstract

AbstractThe strategy used for the stereospecific synthesis of benzofused octams as cepham analogs was the conversion of a 3,4‐dihydrothioisocarbostyril to a thioimidate, cycloaddition reaction to form a fused β‐lactam and subsequent removal of the alkylthio group by Raney nickel hydrogenolysis. Using azidoacetyl chloride for forming the β‐lactam and following known procedures, an amido side chain was generated. Two of the carba analogs of cephalosporin so produced showed low levels of antibacterial activity against a number of gram positive and gram negative organisms.