Stereospecific synthesis of chiral precursors of thienamycin from L-Threonine |
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Authors: | Masao Shiozaki Noboru Ishida Tetsuo Hiraoka Hiroshi Maruyama |
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Affiliation: | Chemical Research Laboratories, Sankyo Company Limited, Hiromachi 1-2-58, Shinagawa-ku, Tokyo 140 Japan |
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Abstract: | L-Threonine was transformed, stereospecifically, to a versatile β-lactam (5a) in 3 steps. This β-lactam was further converted to a key intermediate (25) for the synthesis of thienamycin and its biologically active analogues. Furthermore, the compound 5a was changed to iodides (18 and 23), cyanides (19 and 24), chloromethylketone (26) and aldehydes (30 and 31) which appear to have a latent potential as precursors for the syntheses of the carbapenems. |
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