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β-Lactam synthesis: Chemospecific sulfonation and cyclization of the β-hydroxyvaline nucleus

✍ Scribed by W.A Slusarchyk; T Dejneka; J Gougoutas; W.H Koster; D.R Kronenthal; M Malley; M.G Perri; F.L Routh; J.E Sundeen; E.R Weaver; R Zahler; J.D Godfrey Jr.; R.H Mueller; D.J Von Langen

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

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✦ Synopsis

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 sterically hindered B-hydroxy amino acid. Competitive rearrangement of 2 also occurs during cyclization providing isomeric j3-lactam 5.

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