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Diastereoselective Flexible Synthesis of Carbocyclic C-Nucleosides
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SYSNO ASEP 0476449 Document Type J - Journal Article R&D Document Type Journal Article Subsidiary J Článek ve WOS Title Diastereoselective Flexible Synthesis of Carbocyclic C-Nucleosides Author(s) Maier, L. (CZ)
Khirsariya, P. (CZ)
Hylse, O. (CZ)
Adla, S.K. (CZ)
Cernova, L. (CZ)
Poljak, M. (CZ)
Krajčovičová, S. (CZ)
Weis, E. (CZ)
Drápela, Stanislav (BFU-R) ORCID
Souček, Karel (BFU-R) RID, ORCID
Paruch, K. (CZ)Number of authors 11 Source Title Journal of Organic Chemistry. - : American Chemical Society - ISSN 0022-3263
Roč. 82, č. 7 (2017), s. 3382-3402Number of pages 21 s. Publication form Print - P Language eng - English Country US - United States Keywords mitsunobu ; catalysis ; alcohols Subject RIV CC - Organic Chemistry OECD category Organic chemistry Institutional support BFU-R - RVO:68081707 UT WOS 000398986000004 DOI 10.1021/acs.joc.6b02594 Annotation Carbocyclic C-nucleosides are quite rare. Our route enables flexible preparation of three classes of these nucleoside analogs from common precursors properly substituted cyclopentanones, which can be prepared racemic (in six steps) or optically pure (in ten steps) from inexpensive norbornadiene. The methodology allows flexible manipulation of individual positions around the cyclopentane ring, namely highly diastereoselective installation of carbo- and heterocyclic substituents at position 1', orthogonal functionalization of position 5', and efficient inversion of stereochemistry at position 2'. Newly prepared carbocyclic C-analog of tubercidine, profiled in MCF7 (breast cancer) and HFF1 (human foreskin fibroblasts) cell cultures, is less potent than tubercidine itself, but more selectively toxic toward the tumorigenic cells. Workplace Institute of Biophysics Contact Jana Poláková, polakova@ibp.cz, Tel.: 541 517 244 Year of Publishing 2018
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