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Communication | Regular issue | Vol 14, No. 4, 1980, pp.403-406
Published online, 1st January, 1970
DOI: 10.3987/R-1980-04-0403
An Improved Synthesis of an Intermediate for Thienamycin Synthesis

Tetsuji Kametani,* Takayasu Nagahara, Yukio Suzuki, Shuichi Yokohama, Shyh-Pyng Huang, and Masataka Ihara

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


Methyl 3-amino-5-hydroxy-1,1-dimethoxyhexane-4-carboxylate (2) was converted into trans- and cis-azetidinones (3 and 10) by sequential trimethylsilylation, cyclisation with Grignard reagent, and deblocking. The corresponding tert-butyl ester (15), prepared via the isoxazoline derivative (13), was selectively transformed into the trans-β-lactam (3), a synthetic intermediate of thienamycin, by the same reaction sequence.