Efficient synthesis of hydroxy-substituted cispentacin derivatives

Gabriella Benedek, Márta Palkó, Edit Wéber, Tamás A. Martinek, Eniko Forró, Ferenc Fülöp

Research output: Article

32 Citations (Scopus)

Abstract

Starting from N-protected cis- and trans-2-aminocyclopent-3-enecarboxylic acid derivatives, isomers of 2-amino-3-hydroxycyclopentanecarboxylic acid (8 and 12) were prepared via oxazoline intermediates, whereas the stereoisomeric 2-amino-3,4-dihydroxycyclopentanecarboxylic acids 14 and 17 were synthesized by OsO4-catalyzed oxidation. The enantiomers of 8 and 14 were also prepared by the same pathway. The structures, stereochemistry and relative configurations of the synthesized compounds were proved by NMR spectroscopy.

Original languageEnglish
Pages (from-to)3724-3730
Number of pages7
JournalEuropean Journal of Organic Chemistry
Issue number21
DOIs
Publication statusPublished - júl. 1 2008

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry

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