Stereospecific synthesis and antibiotic activity of some cephalosporin analogs

The 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.