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Communication | Regular issue | Vol 16, No. 5, 1981, pp.767-770
Published online, 1st January, 1970
DOI: 10.3987/R-1981-05-0767
An Asymmetric Synthesis for the Synthetic β-Lactam Intermediate of Thienamycin via Isoxazoline Derivative

Tetsuji Kametani,* Takayasu Nagahara, and Masataka Ihara

*Pharmaceutical Institute, Tohoku University, Aobayama, Sendai 980-8578, Japan


An asymmetric synthesis for the synthetic intermediate to thienamycin was examined via an isoxazoline derivative prepared by 1,3-dipolar cycloaddition between the nitrile oxide and menthyl crotonate. 3(R)-[1’(S)-Hydroxyethyl]-4(S)-(2’,2’-dimethoxyethyl)-2-azetidinone (6B) and its derivative (9B) showed a positive Cotton effect at 214 ~ 213 nm in the cd spectra, respectively.