There has been considerable recent interest in the synthesis of monocyclic 6-lactams as a result of the isolation, from fermentation cultures, of antibiotics such as nocardicin A (1j1,2.3 and the observation of the remarkably high antimicrobial activity associated with these products.'
A convenient synthesis of the β-lactam ring by 3 + 1 cyclization
✍ Scribed by Koichi Hirai; Yuji Iwano
- Publisher
- Elsevier Science
- Year
- 1979
- Tongue
- French
- Weight
- 174 KB
- Volume
- 20
- Category
- Article
- ISSN
- 0040-4039
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📜 SIMILAR VOLUMES
The cyclization of hydroxamate 1 unexpectedly afforded two isomeric @lactams 2 and 1. The mechanism for the formation of 2 has been shown by carbon-13 labeling to involve a novel 1,2-acyl migration-cyclization process.
Summaryz Azetidine-2,3-dionee can be conveniently synthesized by mild hydrolysis of the product of the reaction between a-phenylthio-&la&ems and sulfuryl chloride.
Alcohols 4\_ and s prepared from 3 underwent completely stereospecific etherification to give l-oxacephams 2 and s which were converted into the 1-oxacephem nucleus 2 via kaand lc. Functionalization at C-3' in 6 and &was unsuccessful. Since 7a-methoxy-1-oxacephem & (6059-S) was found to be a highly