Nuclear analogs of β-lactam antibiotics. VIII. Synthesis of 3-acetoxymethyl-Δ3-O-2-isocephems
- 15 May 1978
- journal article
- research article
- Published by Canadian Science Publishing in Canadian Journal of Chemistry
- Vol. 56 (10) , 1335-1341
- https://doi.org/10.1139/v78-221
Abstract
The synthesis of 7.beta.-(-2''-thienylacetamido)-3-acetoxymethyl-.DELTA.3-O-2-isocephem-4-carboxylic acid (17) is described. Treatment of enol mesylate or triflate with triethylamine gave the allene, which gave the diiodide upon treatment with iodine. The diiodide gave benzyl 7.beta.-azido-3-acetoxymethyl-.DELTA.3-O-2-isocephem-4-carboxylate (12) on treatment with potassium acetate. Hydrogenolysis of 12 gave the amino acid, which was converted to (17) upon treatment with 2-thienylacetyl chloride. Resolution of 17 into its optical antipodes was carried out. The antibiotic [antibacterial] activities of racemic 17 and each antipode is compared to that of cephalothin. Antibiotic activity was found to reside in the dextrorotatory isomer.This publication has 2 references indexed in Scilit:
- Nuclear analogs of β-lactam antibiotics. VII. Synthesis of 2-isocephemsCanadian Journal of Chemistry, 1977
- Nuclear analogs of β-lactam antibiotics. VI. Synthesis of N-2-isocephemsCanadian Journal of Chemistry, 1977