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Synthesis of Cephalosporin‐Type Antibiotics by Coupling of Their β‐Lactam Nucleus and Racemic Amino Acid Side Chains Using a Clathration‐Induced Asymmetric Transformation
Author(s) -
Kemperman Gerardus J.,
Zhu Jie,
Klunder Antonius J. H.,
Zwanenburg Binne
Publication year - 2001
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/1099-0690(200105)2001:10<1817::aid-ejoc1817>3.0.co;2-c
Subject(s) - chemistry , cephalosporin antibiotic , epimer , cephalosporin , cephradine , side chain , lactam , diastereomer , cephalosporin c , stereochemistry , transformation (genetics) , antibiotics , organic chemistry , biochemistry , polymer , gene
The cephalosporin‐type antibiotics Cephalexin, Cephradine and Cefadroxil have been prepared by coupling of their β‐lactam nucleus and racemic amino acid side chain precursors. The initially obtained mixture of cephalosporin epimers is subjected to a clathration‐induced asymmetric transformation which results in the epimerization of the epi ‐cephalosporin into the cephalosporin with the correct diastereomeric configuration.