(+)-(5R,6S)-2-(1′-Aminoalkyl)-6-(hydroxyalkyl)penem-3-carboxylic Acids |
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Authors: | Marc Lang,Ernst Hungerbü hler,Peter Schneider,Riccardo Scartazzini,Werner Tosch,Edward A. Konopka,Oto Zak |
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Abstract: | In continuation of our work on penem antibiotics, novel chiral (5R,6S)-2-(1′-aminoalkyl)-6-(hydroxyalkyl)-derivatives 1 have been synthesized by two essentially different strategies. Whereas the starting materials for 1a - f , azetidinones 2 and 5 , were obtained from chiral building blocks (6-aminopenicillanic acid and L-threonine, resp.), the one for 1g , azetidinone 9 , was derived from racemic 4-acetoxyazetidinone and, as chiral auxiliary, (2R)-2-mercaptopropan-1-ol. The 2-aminomethyl derivatives 1a (CGP 30 779) and 1f (CGP 31 608) proved the most potent compounds in the antibacterial tests in vitro and showed a well-balanced spectrum of activity by comparison with that of established β-lactams. |
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