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An enantioselective approach to carbapenem antibiotics: formal synthesis of (+)-thienamycin

โœ Scribed by David J. Hart; Deok-Chan Ha

Publisher
Elsevier Science
Year
1985
Tongue
French
Weight
219 KB
Volume
26
Category
Article
ISSN
0040-4039

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โœฆ Synopsis

An enantioselective synthesis of intermediates in syntheses of thienamycin (15) and epithienamycin-C (16) is described. Several years ago we reported that N-trimethylsilyl imines react with ester enolates to afford l-unsubstituted-B-lactams. 1 We also showed that ethyl B-hydroxybutyrate would serve as the ester component in this reaction, resulting in a direct route to 3-(1-hydroxyethyl)-2azetidinones. 2 This letter presents our initial efforts to apply these observations to the

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An efficient enantioselective synthesis
An efficient enantioselective synthesis of the carbapenam-2-one system. An approach to (+)-thienamycin and related carbapenems
โœ A.I. Meyers; Thomas J. Sowin; Stefan Scholz; Yasutsugu Ueda ๐Ÿ“‚ Article ๐Ÿ“… 1987 ๐Ÿ› Elsevier Science ๐ŸŒ French โš– 215 KB

Cycloaddition of the enantiomeric 4-acetoxy-2-azetidinone (5) with the 2-siloxy-1,3butadiene (8) gives the carbacephem 9 which is cleaved via ozone and cyclized to the carbapenem system (+)-13 in 30% overall yield. The extensive activity directed toward the carbapenem systems (1, 2) due to their hig