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Synthetic study of 1-substituted carbapenem antibiotics

✍ Scribed by Tomoyuki Shibata; Kimio Iino; Teruo Tanaka; Toshihiko Hashimoto; Yukiko Kameyama; Yukio Sugimura

Book ID: 104226849
Publisher: Elsevier Science
Year: 1985
Tongue: French
Weight: 255 KB
Volume: 26
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(00)94938-4

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✦ Synopsis

Total synthesis of l-substituted carbapenems is described.

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The key s the reaction of acetoxyazetidinone (1) with ketene silyl acetal (8). l-S-Methyl RS-533 (176) Is highly resistant to enzymatic hydrolysis by DHP-I, and shows strong antibacterial activity and good bioavailability.

l-a-Methyl X-533 (*), l-methoxy RS-533 ( ) and l,l-dimethyl are also rather resistant to DHP-I but showed relatively weak antibacterial activities. The detailed antibacterial activities of these l-substituted RS-533 will be reported elsewhere.

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