Abstract
Synthesis and structure determination of diastereomeric carbapenems in the AdNE-reaction of (±)-4,4-dimethyl-3-mercaptodihydrofuran-2(3H)-one with chiral carbapenem enol phosphate
Highlights
Though carbapenems are resistant to the majority of lactamases, Zn-dependent βlactamases (NDM-1 and others) destroy the β-lactam ring by hydrolysis, thereby inactivating the antibiotic.[7,8,9]
The synthesis and introduction of new types of carbapenems with more stable structures are relevant in medicine in the fight against infectious diseases
We report the synthesis of a new carbapenem 1 by coupling of the well-known carbapenem 210 with thiol 3 which was obtained from pantolactone for the first time
Summary
Carbapenems are known as efficient broad-spectrum low-toxic antibiotics in the series of antimicrobial agents belonging to the β-lactam class.[1,2,3] A key problem in antibiotic therapy is that microbes develop new strains that are resistant to the drug, which eventually results in a decrease or complete loss of the drug activity.[4,5,6] Though carbapenems are resistant to the majority of lactamases (i.e. serine β-lactamases), Zn-dependent βlactamases (NDM-1 and others) destroy the β-lactam ring by hydrolysis, thereby inactivating the antibiotic.[7,8,9] For this reason, the synthesis and introduction of new types of carbapenems with more stable structures are relevant in medicine in the fight against infectious diseases.In this work, we report the synthesis of a new carbapenem 1 by coupling of the well-known carbapenem 210 with thiol 3 which was obtained from pantolactone for the first time. Considering that in the reaction of (±)-3 with 2, the predominant formation of 1a is observed at first, the S-configuration of the chiral center should be assigned to the residual thiol (Scheme 2). In the case of S-3, doublet signals of both enantiomers are observed in the 1H NMR spectra upon addition of the europium complex (Figure 8), which indicates the high enantiomeric purity of the thiol (-)-3 obtained (ee=89%).
Sign-in/Register to view highlights & summary Talk to us
Join us for a 30 min session where you can share your feedback and ask us any queries you have
Schedule a callSimilar Papers
Disclaimer: All third-party content on this website/platform is and will remain the property of their respective owners and is provided on "as is" basis without any warranties, express or implied. Use of third-party content does not indicate any affiliation, sponsorship with or endorsement by them. Any references to third-party content is to identify the corresponding services and shall be considered fair use under The CopyrightLaw.
