Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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Synthetic Studies on Penems and Carbapenems(IV). Practical Preparation of (3R,4R)-4-Acetoxy-3-[(1R)-1-hydroxyethyl]azetidin-2-one Derivatives from 6-Aminopenicillanic Acid

  • Goo, Yang-Mo (Department of Pharmacy, Seoul National University) ;
  • Lee, Young-Bok (Department of Pharmacy, Seoul National University) ;
  • Kim, Ho-Hyun (Department of Chemistry, Seoul National University) ;
  • Lee, Youn-Young (Department of Chemistry, Seoul National University) ;
  • Lee, Woo-Young (Department of Chemistry, Seoul National University)
  • Published : 1987.02.20
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Abstract

Preparation of optically pure (3R, 4R)-4-acetoxy-3-[(1R)-1-hydroxyethyl]azetidin-2-o ne derivatives, which can be employed as starting materials for synthesis of carbapenem and penem antibiotics, was established in high efficiency from 6-amino-penicillanic acid (6-APA). 6-APA was diazotized and brominated to give 6, 6-dibromopenicillanic acid and its methyl ester was metalated with methylmagnesium bromide and condensed with acetaldehyde. The product, methyl 6-bromo-6-(1-hydroxyethyl)penicillanate was reduced with Zn-$NH_4Cl-NH_4OH$-acetone efficiently to give methyl 6-(l-hydroxyethyl)-penicillanate, which was protected either with ${\beta},{\beta},{\beta}$ -trichloroethoxycarbonyl group or with t-butyldimethylsilyl group. The thiazolidine rings of these compounds were cleaved by treatment of mercury(II) acetate in acetic acid and permangante in acetone in sequence to afford the desired optically pure final products.

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  2. Preparations of two pivotal intermediates for the synthesis of 1-β-methyl carbapenem antibiotics vol.52, pp.2, 1987, https://doi.org/10.1016/0040-4020(95)00842-x
  3. Novel Stereoselective Synthesis of 4-Acetoxyazetidinone from Methyl 6,6-Dibromopenicillanate: Key Intermediate for the Preparation of Carbapenem Antibiotics vol.39, pp.22, 1987, https://doi.org/10.1080/00397910902883637