Chemical and Pharmaceutical Bulletin p. 1381 - 1387 (1994)
Update date:2022-09-26
Topics:
Sunagawa
Sasaki
Matsumura
Goda
Tamoto
An efficient synthesis of 1β-methylcarbapenem from the 1-(2- oxoazetidinyl)acetate 8 was developed by application of the Dieckmann reaction. Dieckmann-type cyclization of 8 and conversion to the enolphosphate 10 were achieved without epimerization to the 1α-methyl isomer in a one-pot procedure. Treatment with the mercaptan 22 after the phosphorylation resulted in a practical one-pot preparation of the 1β-methylcarbapenem derivative 23 from 8.
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