Synthesis of 2-(Heteroarylthiomethyl)-1β-methylcarbapenem via Propargylation of 4-Acetoxy-2-azetidinone with 3-Methyl-1-tributylstannylallene

Jun-ichi HARUTA; Koichi NISHI; Kazumi KIKUCHI; Satoshi MATSUDA; Yasumitsu TAMURA; Yasuyuki KITA

doi:10.1248/cpb.37.2338

Jun-ichi HARUTA, Koichi NISHI, Kazumi KIKUCHI, Satoshi MATSUDA, Yasumitsu TAMURA, Yasuyuki KITA

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Keywords: propargylation, 3-methyl-1-tributylstannylallene, 4-acetoxy-2-azetidinone, 4[(1S)-1-methyl-2-propynyl]-2-azetidinone, 2-(heteroarylthiomethyl)-1β-mehylcarbapenem

JOURNAL FREE ACCESS

1989 Volume 37 Issue 9 Pages 2338-2343

DOI https://doi.org/10.1248/cpb.37.2338

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Abstract

The key intermediate in the synthesis of 1β-methylcarbapenem, (3S, 4R)-3-[(1R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-[(1S)-1-methyl-2-propynyl]-2-azetidinone (5β), was prepared by propargylation of (3R, 4R)-4-acetoxy-3-[(1R)-1-(tert-butyldimethylsilyloxy)ethyl]-2-azetidinone (3) with 3-methyl-1-tributylstannylallene (4) in the presence of a Lewis acid and successfully converted to a novel 2-(heteroarylthiomethyl)-1β-methylcarbapenem (2).

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