75321-08-3Relevant articles and documents
A catalytic asymmetric route to carbapenems
Bodner, Micah J.,Phelan, Ryan M.,Townsend, Craig A.
, p. 3606 - 3609 (2011/03/17)
Image Presented 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.
Stereoselective reactions. XX. Synthetic studies on optically active β-lactams. III. Stereocontrolled synthesis of chiral intermediate to (+)-thienamycin from D-glucose
Ikota,Yoshino,Koga
, p. 2201 - 2206 (2007/10/02)
A chiral key intermediate (19a) for the synthesis of (+)-thienamycin was synthesized starting from D-glucose. The enol ether 13, obtained from the ketone 11 by Horner-Wittig reaction, was transformed to the corresponding methyl ester 16 by pyridinium chlorochromate oxidation or by employing the Wacker process. The ester 16 was further converted to the β-lactam 19a, which is a useful chiral precursor to (+)-thienamycin.
A Stereocontrolled Synthesis of (+)-Thienamycin
Salzmann, Thomas N.,Ratcliffe, R. W.,Christensen, B. G.,Bouffard, F. A.
, p. 6161 - 6163 (2007/10/02)
-
