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 synthe...

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Bibliographic Details
Published in:European Journal of Organic Chemistry 2008-07, Vol.2008 (21), p.3724-3730
Main Authors: Benedek, Gabriella, Palkó, Márta, Wéber, Edit, Martinek, Tamás A., Forró, Enikő, Fülöp, Ferenc
Format: Article
Language:English
Subjects:
Amino acids
Diastereoselectivity
Hydroxycispentacin
Hydroxylation
Regioselectivity
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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. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008) New mono‐ and dihydroxy‐substituted cispentacin derivatives have been prepared with functionalization of the olefinic bond of the cis‐2‐aminocyclopent‐3‐enecarboxylic acid. The enantiomers of these molecules were also prepared by the same pathway. The structures, stereochemistry and relative configurations of the synthesized compounds were proved by NMR spectroscopy.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.200800345