Nuclear analogs of β-lactam antibiotics. II. Synthesis of O-2-isocephems
- 1 February 1977
- journal article
- research article
- Published by Canadian Science Publishing in Canadian Journal of Chemistry
- Vol. 55 (3) , 484-507
- https://doi.org/10.1139/v77-070
Abstract
The preparation by total synthesis of a new class of .beta.-lactam antibiotics is reported. Conversion of alcohol 1b to its mesylate followed by hydrolysis of the acetal to the enol 1b and base-catalyzed ring closure gave benzyl 7-.beta.-azido-.DELTA.3-O-2-isocephem-4-carboxylate. Similarly prepared were the 3-methyl, 3-benzyl, and 3-phenethyl analogs. Reduction of the azides followed by coupling of the resultant amines with phenoxyacetic acid and removal of the benzyl groups by hydrogenolysis gave acids which exhibited high antibacterial activity. Structural assignments to the O-2-isocephems which were made on the basis of their spectral characteristics (IR, UV and NMR) are discussed.This publication has 1 reference indexed in Scilit:
- Studies in Chemotherapy. X. Antithyroid Compounds. Synthesis of 5- and 6- Substituted 2-Thiouracils from β-Oxoesters and Thiourea1Journal of the American Chemical Society, 1945