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The synthesis of β-lactams by the cyclization of β-halopropionamides

✍ Scribed by Harry H. Wasserman; Dennis J. Hlasta; Alan W. Tremper; James S. Wu

Publisher
Elsevier Science
Year
1979
Tongue
French
Weight
192 KB
Volume
20
Category
Article
ISSN
0040-4039

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✦ Synopsis

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.'

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✍ W.A Slusarchyk; T Dejneka; J Gougoutas; W.H Koster; D.R Kronenthal; M Malley; M. 📂 Article 📅 1986 🏛 Elsevier Science 🌐 French ⚖ 267 KB

The intramolecular cyclization of "hydroxamate" 2 using Mitsunobu conditions was inefficient for the formation and isolation of the C-4 dimethyl monobactam 3. However, chemospecific 0-sulfonation of 2 and subsequent cyclization with base provides a useful method for &lactam synthesis from a sterical