A selective synthesis of fluorinated cispentacin derivatives

Loránd Kiss, Melinda Nonn, Eniko Forrõ, Reijo Sillanpää, Santos Fustero, Ferenc Fülöp

Research output: Contribution to journalArticle

16 Citations (Scopus)

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. 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.

Original languageEnglish
Pages (from-to)4070-4076
Number of pages7
JournalEuropean Journal of Organic Chemistry
Volume2014
Issue number19
DOIs
Publication statusPublished - Jul 2014

Keywords

  • Amino acids
  • Carbocycles
  • Fluorine
  • Hydroxylation
  • Stereoselective synthesis

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry

Fingerprint Dive into the research topics of 'A selective synthesis of fluorinated cispentacin derivatives'. Together they form a unique fingerprint.

  • Cite this