Open AccessNuclear analogs of β-lactam antibiotics. XII. 2-Oxodesthiocephalosporins
Author(s) -
Alain Martel,
Terrence W. Doyle,
BingYu Luh
Publication year - 1979
Publication title -
canadian journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.323
H-Index - 68
eISSN - 1480-3291
pISSN - 0008-4042
DOI - 10.1139/v79-100
Subject(s) - chemistry , allylic rearrangement , allylic alcohol , lactam , cephalosporin , antibiotics , stereochemistry , beta lactam , alcohol , cephalosporin antibiotic , organic chemistry , catalysis , biochemistry
Epoxidation of Δ 2 -1-carbacephems 2 followed by base treatment gave the allylic alcohols 4. Oxidation of 4 gave the 2-keto-Δ 3 -carbacephem 9 which could be reduced to the isomeric allylic alcohol 7. Conversion of these intermediates to a series of biologically active cephalosporin analogs 13g–l and 14 is described.
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