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A Modular Approach to Aryl-C-ribonucleosides via the Allylic Substitution and Ring-Closing Metathesis Sequence. A Stereocontrolled Synthesis of All Four alpha-/beta- and D-/L-C-Nucleoside Stereoisomers
- 1.0368189 - ÚOCHB 2012 RIV US eng J - Journal Article
Štambaský, J. - Kapras, V. - Štefko, Martin - Kysilka, O. - Hocek, Michal - Malkov, A. V. - Kočovský, P.
A Modular Approach to Aryl-C-ribonucleosides via the Allylic Substitution and Ring-Closing Metathesis Sequence. A Stereocontrolled Synthesis of All Four alpha-/beta- and D-/L-C-Nucleoside Stereoisomers.
Journal of Organic Chemistry. Roč. 76, č. 19 (2011), s. 7781-7803. ISSN 0022-3263. E-ISSN 1520-6904
R&D Projects: GA MŠMT LC512; GA AV ČR IAA400550902
Institutional research plan: CEZ:AV0Z40550506
Keywords : C-nucleosides * allylic substitution * metathesis * dihydroxylation
Subject RIV: CC - Organic Chemistry
Impact factor: 4.450, year: 2011
Iridium(I)-catalyzed allylation of the enantiopure monoprotected copper(I) alkoxides with enantiopure allylic carbonates has been developed as the key step in a new approach to C-nucleoside analogues. The synthesis continued by ring-closing metathesis and dihydroxylation. This approach allows the synthesis of all four combinations of alpha/beta and D/L-diastereoisomers.
Permanent Link: http://hdl.handle.net/11104/0202600
Number of the records: 1