6533b7d1fe1ef96bd125c118
RESEARCH PRODUCT
A Selective Synthesis of Fluorinated Cispentacin Derivatives
Melinda NonnMelinda NonnReijo SillanpääEnikő ForróSantos FusteroLoránd KissFerenc FülöpFerenc Fülöpsubject
Hydroxylationchemistry.chemical_classificationchemistry.chemical_compoundchemistryBicyclic moleculeOrganic ChemistryOrganic chemistryStereoselectivityCispentacinPhysical and Theoretical ChemistryLevorotatoryDeoxygenationAmino aciddescription
A facile selective method has been developed for the synthesis of new fluorine-containing cispentacin stereoisomers. Mono- and difluorinated cispentacin derivatives were synthetized from a bicyclic β-lactam in five or six steps involving a regio- and stereoselective hydroxylation through iodooxazoline formation, followed by deoxygenation by fluorination. Starting from an enantiomerically pure bicyclic β-lactam obtained by enzymatic resolution of the racemic compound, an enantiodivergent procedure allowed the preparation of both dextro- and levorotatory difluorinated cispentacins.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2014-05-08 | European Journal of Organic Chemistry |