• Bulletin of the Korean Chemical Society
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• v.31 no.9
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• pp.2683-2684
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• 2010

• Bulletin of the Korean Chemical Society
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• v.18 no.9
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• pp.1032-1034
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• 1997

• Bulletin of the Korean Chemical Society
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• v.19 no.12
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• pp.1294-1295
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• 1998

• Bulletin of the Korean Chemical Society
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• v.27 no.8
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• pp.1164-1170
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• 2006

The synthesis of a new series of 1$\beta$-methylcarbapenems having 5-($\alpha,\beta$-disubstituted ethyl)pyrrolidine moiety is described. Their in vitro antibacterial activities against both Gram-positive and Gram-negative bacteria were tested and the effect of substituents on the pyrrolidine ring was investigated. A particular compound (VIh) having $\alpha$-hydroxy-$\beta$-piperazinylethyl substituted moiety showed the most potent activity.

• Bulletin of the Korean Chemical Society
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• v.27 no.5
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• pp.705-712
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• 2006

The synthesis of a new series of 1 $\beta$-methylcarbapenems having 5-(1,2-disubstituted ethyl)pyrrolidine moiety are described. Their in vitro antibacterial activities against both Gram-positive and Gram-negative bacteria were tested and the effect of substituents on the pyrrolidine ring was investigated. Among them, compound (IIIc) having 1-methoxyimino-2-hydroxyethyl moiety showed the most potent antibacterial activity.

• YAKHAK HOEJI
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• v.47 no.6
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• pp.450-455
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• 2003

Synthesis of (lR,5S,6S)-6-[(lR)-1-hydroxyethyl] -2-[(3S,5S)-5-(2-ethoxycarbonyl-1-moxy(hydroxy)iminoethyl)pyrrolidine-3-ylthio]-1-methylcarbapen-2-em-3-carboxylic acids (10a,l0b) were described. Methyl(2S,4S)-4-tritylthio-1-(allyloxycarbonyl)pyrrolidine-2-carboxyla late (I) was prepared from trans-4-hydroxy-L-proline with (2S,4R)-abs olute configuration as starting material. (2S,4S)-1-allyloxycarbonyl-2-(2-ethoxycarbonyl-hydroxy(methoxy )iminoethyl)-4-mercapto- pyrrolidines (6,7) were obtained from the tritylthio compound (I). (lR,5S,6S)-6-[(lR)-1-hydroxyethyl]-2-[(3S,5S)-5-(2-ethoxycarbonyl-1-methoxy(hydroxy)imino-ethyl)pyrrolidine-3-ylthio]-1-methylcarbapem-2-em-3-carboxylic acids (10a,10b) were obtained by the coupling reaction with carbapenem diphenylphosphates (8) and pyrrolidine-thiol moiety (6,7). Their in vitro antibacterial activities against both Gram-positive and Gram-negative were tested. Compounds ( 10a,10b) showed potent antibacterial activity except pseudomonas aerusinosa.