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One-step synthesis of oxazolinoazetidinones from penicillin sulfoxides: potential intermediates for 1-oxacephem synthesis

✍ Scribed by Sadao Yamamoto; Susumu Kamata; Nobuhiro Haga; Yoshio Hamashima; Wataru Nagata

Book ID: 104234167
Publisher: Elsevier Science
Year: 1981
Tongue: French
Weight: 231 KB
Volume: 22
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(01)81835-9

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✦ Synopsis

Reaction of penicillin sulfoxides with a tervalent phosphorous compound in the presence of a catalytic amount of squaric acid gave oxazolinoazetidinones, potential intermediates for synthesis of 1-oxacephems, in good yields. 2!3-Chloromethyl-and 6cr-methoxypenicillin sulfoxides also undergo this reaction. The reaction contrasts with the well-known Cooper reaction which usually gives thiazolinoazetidinones. Recently our research group discovered a clinically useful fl-lactam antibiotic ') (code-

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