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Desulfation and rearrangement of tigemonam to an isoxazolidin‐5‐one and the synthesis of the rearrangement product
Author(s) -
Singh Janak,
Kissick Thomas P.,
Fox Rita,
Kocy Octavian,
Mueller Richard H.
Publication year - 1989
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570260104
Subject(s) - chemistry , lactam , product (mathematics) , cope rearrangement , rearrangement reaction , stereochemistry , carroll rearrangement , combinatorial chemistry , sigmatropic reaction , organic chemistry , catalysis , geometry , mathematics
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.