A Selective Synthesis of Fluorinated Cispentacin Derivatives

Kiss, Lorand and Nonn, Melinda and Forró, Enikő and Sillanpää, Reijo and Fustero, Santos and Fülöp, Ferenc (2014) A Selective Synthesis of Fluorinated Cispentacin Derivatives. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY. pp. 4070-4076. ISSN 1434-193X

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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.

Item Type: Article
Uncontrolled Keywords: Keywords: Stereoselective synthesis, Hydroxylation, Amino acids, Carbocycles, Fluorine
Subjects: Q Science / természettudomány > QD Chemistry / kémia > QD04 Organic chemistry / szerves kémia
Depositing User: Dr Loránd Kiss
Date Deposited: 11 Sep 2014 12:35
Last Modified: 12 Sep 2014 06:23

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