1989 Volume 37 Issue 9 Pages 2298-2302
Various kinds of 1, 2-disubstituted-1-carbacephems were synthesized by employing several electrophilic reactions (e.g. oxidation, halogenation, halogenohydrination) toward the aldehyde 2 followed by cyclization, and also from 1, 2-dehydro-1-carbacephem 10. The stereochemistry of the 1, 2-disubstituted-1-carbacephems prepared was determined by proton nuclear magnetic resonance (1H-NMR) analysis. The diol 4a, chlorohydrin 15a and bromohydrin 17a were converted to the corresponding 7-N-acylated compounds 27a-c. Antibacterial activities of 27a-c, however, were rather low compared with those of KT 3919 (non-substituted carbocephem) and KT 3933 (2α-hydroxy carbacephem), which are the racemates of KT 3767 and KT 3937, respctively.
