Stereo- and regiocontrolled syntheses of exomethylenic cyclohexane β-amino acid derivatives

Loránd Kiss, Eniko Forró, György Orsy, Renáta Ábrahámi, Ferenc Fülöp

Research output: Article

6 Citations (Scopus)

Abstract

Cyclohexane analogues of the antifungal icofungipen [(1R,2S)-2-amino-4-methylenecy clopentanecarboxylic acid] were selectively synthesized from unsaturated bicyclic β-lactams by transformation of the ring olefinic bond through three different regio- and stereocontrolled hydroxylation techniques, followed by hydroxy group oxidation and oxo-methylene interconversion with a phosphorane. Starting from an enantiomerically pure bicyclic β-lactam obtained by enzymatic resolution of the racemic compound, an enantiodivergent procedure led to the preparation of both dextro- and levorotatory cyclohexane analogues of icofungipen.

Original languageEnglish
Pages (from-to)21094-21101
Number of pages8
JournalMolecules
Volume20
Issue number12
DOIs
Publication statusPublished - nov. 27 2015

ASJC Scopus subject areas

  • Analytical Chemistry
  • Chemistry (miscellaneous)
  • Molecular Medicine
  • Pharmaceutical Science
  • Drug Discovery
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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