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Communication | Regular issue | Vol 16, No. 1, 1981, pp.53-63
Published online, 1st January, 1970
DOI: 10.3987/R-1981-01-0053
Some Aspects for 1,3-Dipolar Cycloaddition Reaction of Nitrile Oxide with Methyl Crotonate in the Synthesis of Carbapenam Antibiotics

Tetsuji Kametani,* Atsushi Nakayama, Yoshito Nakayama, Tsuneko Ikuta, Rumiko Kubo, Eiko Goto, Toshio Honda, and Keiichiro Fukumoto

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


1,3-Dipolar cycloaddition reaction of the nitrile oxides, generated in situ from the nitro compounds (6~9) and phenyl isocyanate, with methyl crotonate afforded the corresponding isoxazolines (10~17) in moderate yields. Hydrogenation of 12, 14 and 16 on platinum oxide gave the amino esters (18 and 20) and the lactam (22), respectively. The amino esters (18 and 20) were converted to the β-lactams (23~26) with ethylmagnesium bromide in tetrahydrofuran. Finally, 3,4-bond formation reaction for the mesyloxy derivative (27) of 24 furnished the carbapenam derivative (28) in good yield.