Efficient synthesis of hydroxy-substituted cispentacin derivatives

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 synthes...

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Bibliographic Details
Main Authors: Benedek György
Palkó Márta
Wéber Edit
Martinek Tamás A.
Forró Enikő
Fülöp Ferenc
Format: Article
Published: Wiley 2008
Series:EUROPEAN JOURNAL OF ORGANIC CHEMISTRY 2008 No. 21
doi:10.1002/ejoc.200800345

mtmt:1128281
Online Access:http://publicatio.bibl.u-szeged.hu/10394
Description
Summary: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. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008).
Physical Description:3724-3730
ISSN:1434-193X