A Selective Synthesis of Fluorinated Cispentacin Derivatives. Issue 19 (8th May 2014)

• Record Type: Journal Article
• Authors: Kiss, Loránd; Nonn, Melinda; Forró, Enikő; Sillanpää, Reijo; Fustero, Santos; Fülöp, Ferenc
• Is Part Of: European journal of organic chemistry. Issue 19(2014)
• Page Start: 4070
• Page End: 4076
• Publication Date: 2014-05-08
• Subjects: Stereoselective synthesis -- Hydroxylation -- Amino acids -- Carbocycles -- Fluorine; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201402121
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract: 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. Abstract : Mono‐ and difluorinated cispentacin derivatives were synthetized from a bicyclic β‐lactam in five or six steps. An enantiodivergent procedure allowed the preparation of both dextro‐ and levorotatory difluorinated cispentacins.