AI Article Synopsis
- The text discusses efficient methods for synthesizing N-acetyl thienamycin and epithienamycin A, focusing on creating three stereocenters in a single reaction.
- It describes how these methods can be used as a model for producing different C-5/C-6 stereoisomers of carbapenems while allowing for independent manipulation of the C-8 stereocenter.
- Additionally, a range of azetidinone precursors has been developed to aid research on the biosynthesis of carbapenem antibiotics.
Article Abstract
Efficient syntheses of N-acetyl thienamycin and epithienamycin A in their readily deprotected form are reported where three contiguous stereocenters are established in a single catalytic asymmetric azetidinone-forming reaction. These examples are a template for synthesizing C-5/C-6 cis or trans carbapenems with independent control of the C-8 stereocenter. A library of oxidatively and sterochemically defined azetidinone precursors to a variety of naturally occurring carbapenems and potential biosynthetic intermediates has been prepared to facilitate studies of carbapenem antibiotic biosynthesis.
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Source |
|---|---|
| http://www.ncbi.nlm.nih.gov/pmc/articles/PMC2736320 | PMC |
| http://dx.doi.org/10.1021/ol901269d | DOI Listing |
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