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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
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SYSNO ASEP 0368189 Document Type J - Journal Article R&D Document Type Journal Article Subsidiary J Článek ve WOS Title 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 Author(s) Štambaský, J. (GB)
Kapras, V. (GB)
Štefko, Martin (UOCHB-X)
Kysilka, O. (CZ)
Hocek, Michal (UOCHB-X) RID, ORCID
Malkov, A. V. (GB)
Kočovský, P. (GB)Number of authors 7 Source Title Journal of Organic Chemistry. - : American Chemical Society - ISSN 0022-3263
Roč. 76, č. 19 (2011), s. 7781-7803Number of pages 23 s. Language eng - English Country US - United States Keywords C-nucleosides ; allylic substitution ; metathesis ; dihydroxylation Subject RIV CC - Organic Chemistry R&D Projects LC512 GA MŠMT - Ministry of Education, Youth and Sports (MEYS) IAA400550902 GA AV ČR - Academy of Sciences of the Czech Republic (AV ČR) CEZ AV0Z40550506 - UOCHB-X (2005-2011) UT WOS 000295302300014 DOI 10.1021/jo201110z Annotation 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. Workplace Institute of Organic Chemistry and Biochemistry Contact asep@uochb.cas.cz ; Kateřina Šperková, Tel.: 232 002 584 ; Viktorie Chládková, Tel.: 232 002 434 Year of Publishing 2012
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