The asymmetric synthesis of β-lactam antibiotics - IV. A formal synthesis of thienamycin.
✍ Scribed by David A. Evans; Eric B. Sjogren
- Publisher
- Elsevier Science
- Year
- 1986
- Tongue
- French
- Weight
- 287 KB
- Volume
- 27
- Category
- Article
- ISSN
- 0040-4039
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✦ Synopsis
Oxidative cleavage of crotonate imide aldol adduct 6b provides the configurationally stable aldehyde 4. Transformation of this aldehyde to enantiomerically pure p-lactams is described.
📜 SIMILAR VOLUMES
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
The application of asymmetric ketene-imine cycloadditions to the first enantioselective synthesis of the carbacephalosporin nucleus is described.
Cycloaddition of nitrone (2) to a-chloroacrylonitrile followed by hydrolysis afforded the isoxazolidinone (I) as a single diastereomer.