Synthetic studies of carbapenem and penem antibiotics. V. Efficient synthesis of the 1β-methylcarbapenem skeleton

DOI: 10.1248/cpb.42.1381

Source and publish data:

Chemical and Pharmaceutical Bulletin p. 1381 - 1387 (1994)

Update date:2022-09-26

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Authors:

Sunagawa

Sasaki Sasaki

Matsumura

Goda Goda

Tamoto Tamoto

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Article abstract of DOI:10.1248/cpb.42.1381

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.

Full text of DOI:10.1248/cpb.42.1381

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