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An enantioselective formal synthesis of thienamycin.

Jamie L BreunigYou-Chen LinJoshua G Pierce
Published in: Tetrahedron letters (2024)
Thienamycin is a carbapenem antibiotic with potent activity against gram-negative and gram-positive bacteria. Due to its promising activity but lack of chemical stability, thienamycin serves as inspiration for new synthetic antibiotic scaffolds. In this study, we report a nine-step enantioselective formal synthesis of thienamycin. Our route utilizes an asymmetric reduction, enabled by NaBH 4 and D-tartaric acid, followed by a series of diastereoselective reactions to access the key azetidinone precursor to thienamycin. This azetidinone precursor could be used as an intermediate to further develop and expand the scope of next-generation beta-lactam antibiotic scaffolds.
Keyphrases
  • gram negative
  • multidrug resistant
  • acinetobacter baumannii
  • drug resistant
  • tissue engineering
  • klebsiella pneumoniae
  • escherichia coli