Desulfation and rearrangement of tigemonam to an isoxazolidin‐5‐one and the synthesis of the rearrangement product
- 1 January 1989
- journal article
- research article
- Published by Wiley in Journal of Heterocyclic Chemistry
- Vol. 26 (1) , 17-21
- https://doi.org/10.1002/jhet.5570260104
Abstract
The β‐lactam antibiotic Tigemonam 2 undergoes desulfation to the N‐hydroxyazetidinone 4, which rearranges to the isoxazolidin‐5‐one 6. The structure of the rearrangement product 6 was confirmed by synthesis.Keywords
This publication has 15 references indexed in Scilit:
- The structures of alkoxycarbonyl, acyl, and sulfonate derivatives of 1-hydroxybenzotriazole: nitrogen- vs oxygen-substitutionThe Journal of Organic Chemistry, 1988
- The mechanisms of heterocyclic ring closuresTetrahedron, 1987
- Rearrangement of N-hydroxy β-lactamsTetrahedron, 1986
- β-Lactam synthesis: Chemospecific sulfonation and cyclization of the β-hydroxyvaline nucleusTetrahedron Letters, 1986
- Studies on monocyclic .BETA.-lactam antibiotics. II. Synthesis and antibacterial activity of 3-acylamino-2-azetidinone-1-oxysulfonic acids.The Journal of Antibiotics, 1985
- Monobactams: Ring Activating N-1-Substituents in Monocyclic b-Lactam AntibioticsHETEROCYCLES, 1984
- O-Sulfated .beta.-lactam hydroxamic acids (monosulfactams). Novel monocyclic .beta.-lactam antibiotics of synthetic originJournal of the American Chemical Society, 1982
- Monocyclic β-lactam antibiotics produced by bacteriaNature, 1981
- Sulfazecin and isosulfazecin, novel β-lactam antibiotics of bacterial originNature, 1981
- Synthesis of Cycloserine and a Methyl AnalogJournal of the American Chemical Society, 1957