Stereocontrolled synthesis of an important intermediate for the preparation of 1. beta.-methylcarbapenem antibiotics

LM Fuentes, I Shinkai, A King, R Purick…

Index: Fuentes, L. M.; Shinkai, I.; King, A.; Purick, R.; Reamer, R. A.; et al. Journal of Organic Chemistry, 1987 ,  vol. 52,  # 12  p. 2563 - 2567

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Citation Number: 36

Abstract

(1R, 11R, 5S, 6S)-2-[(2-N, N-dimethylamino)-2-iminoethyl)-thiol-6-(1-hydroxyethy1)-1- methylcarbapenem (1) possesses improved chemical stability at high concentrations and decreased susceptibility to renal dipeptidase-I while it retains an excellent antibacterial pr~ file.~ Although the synthesis of 1 via the key intermediates 2 and 3a, b has been reported recently: the methodology employed required epimerization, chromatographic separation, ...