1-β-Methylcarbapenem intermediates. Stereoselective synthesis of (3S,4R)-3-[(1R)-1-tert-butyldimethylsilyloxyethyl]-4-[(1R)-3-methoxycarbonyl-1-methyl-2-oxopropyl]azetidin-2-one and its related chemistry

Author:

Endo Masaki,Droghini Robert

Abstract

A chiral intermediate bearing the 1-β-methyl moiety (14a) for 1-β-methylcarbapenem antibiotics (1) was prepared by stereoselective aldol-type reaction between 4-acetoxyazetidinone 3a and the dianion (or corresponding bissilyl enol ether) of a 3-oxopentanoate 12 or 13 in the presence of a metal salt. A major side reaction has also been elucidated.

Publisher

Canadian Science Publishing

Subject

Organic Chemistry,General Chemistry,Catalysis

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