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A catalytic asymmetric route to carbapenems.

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.

SUBMITTER: Bodner MJ

PROVIDER: S-EPMC2736320 | biostudies-literature | 2009 Aug

REPOSITORIES: biostudies-literature

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A catalytic asymmetric route to carbapenems.

Bodner Micah J MJ Phelan Ryan M RM Townsend Craig A CA

Organic letters 20090801 16

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 bios ...[more]

PMID: 19610642

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