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Communication | Regular issue | Vol 27, No. 2, 1988, pp.327-330
Published online, 1st January, 1970
DOI: 10.3987/COM-87-4378
A Chiral Synthesis of the Key Intermediate of 1β-Methylcarbapenem Antibiotic

Masataka Ihara, Masanobu Takahashi, Keiichiro Fukumoto,* and Tetsuji Kametani

*Hoshi University, 2-4-41 Ebara, Shinagawa-ku, Tokyo 142-8501, Japan


The synthetic intermediate, (-)-(3S,4R)-3-[(1R)-1-t- butyldimethylsilyloxyethyl]-4-[(1R)-l-hydroxymethylethyl]azetidin-2-one (2), of 1β -methylcarbapenem antibiotic was synthesized from (S)-methyl 3-hydroxy-2-methylpropionate through the intermolecular nitrone 1,3-dipolor cycloaddition.