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KMID : 0366919960080010007
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Sungkyun Pharmceutical Journal
1996 Volume.8 No. 1 p.7 ~ p.14
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The Synthesis of New Carbapenem Derivatives
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Abstract
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The class of β-lactam containing compounds known as carbapenems has been the focus of countless chemical and biological studies since the naturally occurring structural type was reported in 1976. The discovery of thienamycin, with its extraordinary potent broad-spectrum antibacterial profile, prompted a rigorous search for efficient and general routes to total and partial synthesis of carbapenems.
Wile many strategies of carbapenem construction have been brought to fruit, only two approaches (and conceptually related ones) have emerged with the general usefulness. In fact, they have been applied relentlessly in analogue programs around the world.
This thesis utilize a rhodium catalyzed carbene insertion to establish the bicyclic ring system. The resulting β-keto ester is transformed into carbapenem via vinyl phosphate. Thiol addition-phosphate elimination occurs readily to incorporate the new side-chain thiol.
New carbapenem derivative, {ally(1R, 5S, 6S)-2-(N-carboben-oxycarboxydiethylamido cysteine)-6-[(IR)-1-hydroxyethyl]-1-methyl-carbapen-2-em-3-carboxylate} was synthesized via 10 steps.
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