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A Selective Synthesis of Fluorinated Cispentacin Derivatives
Author(s) -
Kiss Loránd,
n Melinda,
Forró Enikő,
Sillanpää Reijo,
Fustero Santos,
Fülöp Ferenc
Publication year - 2014
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201402121
Subject(s) - chemistry , bicyclic molecule , deoxygenation , stereoselectivity , lactam , enantiomer , hydroxylation , fluorine , stereochemistry , organic chemistry , enzyme , catalysis
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.