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Since the epoch-making discovery of thienamycin,l> 35 carbapenem compounds including epithienamycins,2> olivanates3' and the PS series') have been isolated from many streptomycetes. This family of /-lactam compounds are characterized by a common nucleus of 7-oxo-l-azabicyclo-[3.2.0]hept-2-ene2-carboxylic acid and differ in the C-3 and C-6 side chains and the stereochemistry at C-6 and C-8. Compared with penicillins and cephalosporins, carbapenem compounds have an unexpectedly broad spectrum of potent antimicrobial activity as well as a strong /3-lactamase-inactivating property.'-') However, as they are labile in vitro and in vivo,',11) naturally occurring carbapenem compounds must chemically be modified to clinically useful carbapenem derivatives having satisfactory chemical and biological stability. Recent papers have shown that chemical modifications of carbapenem compounds result in the improvement of their antimicrobial spectrum." 12) In the total synthesis of thienamycin Merck scientists have described the preparation of C-3 substituted carbapenems by treatment of the C-3-O-tosylate or C-3-O-phosphate of carbapenem with thiol compounds.") Recently CORBETT has reported a method of C-3 modification with other thiol groups which is limitedly operable in carbapenem compounds having a double bond in the C-3 side chain such as MM 13902 and epithienamycins B and D.14) In this paper we describe convenient and versatile methods of C-3 displacement which are commonly employable for naturally occurring carbapenem compounds. These methods involve the initial

journal of antibiotics

Chemical modification of carbapenem antibiotics. Versatile methods for displacement of the C-3 sulfur side chain of carbapenems with other thiol groups.