| Autor: |
Conway, Terry Thomas, Lim, Gary, Douotas, James Leslie, Menard, Marcel, Doyle, Terrence William, Rivest, Pierre, Horning, Donald, Morris, Leeson R., Cimon, Denis |
| Zdroj: |
Canadian Journal of Chemistry; May 1978, Vol. 56 Issue: 10 p1335-1341, 7p |
| Abstrakt: |
The synthesis of 7β-(-2′-thienylacetamido)-3-acetoxymethyl-Δ3-O-2-isocepheni-4-carboxylic acid (17) is described. Thus treatment of enol mesylate 3aor triflate 3bwith triethylamine gave the allene 4which gave the diiodide upon treatment with iodine. The diiodide gave benzyl 7β-azido-3-acetoxymethyl-Δ3-O-2-isocephem-4-carboxylate (12) on treatment with potassium acetate in DMF. Hydrogenolysis of 12gave the amino acid 16which was converted to 17upon treatment with 2-thienylacetyl chloride. Resolution of 17into its optical antipodes was carried out. The antibiotic activities of racemic 17and each antipode is compared to that of cephalothin. Antibiotic activity was found to reside in the dextrorotatory isomer. |
| Databáze: |
Supplemental Index |
| Externí odkaz: |
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