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Simple and highly diastereoselective synthesis of a 1β-methylcarbapenem key intermediate involving divalent tin enolates

✍ Scribed by Robert Déziel; Denis Favreau

Publisher
Elsevier Science
Year
1986
Tongue
French
Weight
199 KB
Volume
27
Category
Article
ISSN
0040-4039

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✦ Synopsis

A simple and diastereoselective synthesis of lS-methylcarbapenem key intermediate has been accomplished via a novel C-C bond formation at the C-4 position of 4-acetoxyazetidinone A involving divalent tin enolates of 3-propanoyl thiazolidine and oxazolidine-Z-thiones derivatives. Carbapenems are among the most potent broad spectrum B-lactam antibiotics'. but many of them are readily metabolized by renal dehydropeptidase-I (DHP-I). On the other hand, Merck researchers found that introduction of a methyl substituent at B C-l position of the carbapenem nucleus resulted in an exceptional increase of stability, the lf3-methylcarbapenems 1 and 2 are 2a good examples

. However, only a few papers have appeared regarding the stereoselective intro- .-, duction of the B-methyl substituent'.

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