Tetrahedron letters

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

WA Slusarchyk, T Dejneka, J Gougoutas, WH Koster…

Index: Slusarchyk; Dejneka; Gougoutas; et al. Tetrahedron Letters, 1986 , vol. 27, # 25 p. 2789 - 2792

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Citation Number: 15

Abstract

Abstract: 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.