Total syntheses of (+/-)-1-carbacefoxitin and -cefamandole and (+/-)-1-oxacefamandole.
The total syntheses of the (+/-)-1-carba analogues of cefoxitin (11), 7 alpha-methoxydeacetylcephalothin (5) and cefamandole (31) and the (+/-)-1-oxa analogue of cefamandole (43) are described. Their bioactivity spectra against 14 typical organisms are similar to those of their natural 1-thia counterparts, with the 1-carba compounds somewhat less active and the 1-oxa compound more active than the natural ones.
D001419:Bacteria / Q000187:drug effects; D002435:Cefamandole / Q000031:analogs & derivatives; D002440:Cefoxitin / Q000031:analogs & derivatives / Q000138:chemical synthesis* / Q000494:pharmacology; D002511:Cephalosporins / Q000138:chemical synthesis* / Q000494:pharmacology; D008722:Methods; D008826:Microbial Sensitivity Tests
D002511:Cephalosporins; D002435:Cefamandole; C014384:carbacefoxitin; C014723:oxacefamandole; D002440:Cefoxitin