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Synthesis of Two Precursors of Heterocarbocyclic Nucleoside Analogues
Author(s) -
Abeijón Paula,
Blanco José M.,
Fernández Franco,
García Marcos D.,
López Carmen
Publication year - 2006
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200500515
Subject(s) - chemistry , nucleoside , acetylation , diastereomer , thiophene , organic chemistry , stereochemistry , combinatorial chemistry , biochemistry , gene
The racemic heterobicyclic amino alcohols 6 and 7 , which are of interest as intermediates in the synthesis of nucleoside analogues with heterobicyclic pseudosugars, were efficiently prepared from 2‐thienylsuccinic acid via methyl 4‐hydroxyimino‐5,6‐dihydro‐4 H ‐cyclopenta[ b ]thiophene‐6‐carboxylate [(±)‐ 14 ]. The target compounds were obtainedtogether by direct reduction of (±)‐ 14 with AlH 3 in refluxing THF, and were separated by flash chromatography of their N ‐acetylated derivatives.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)