Diastereoselective Flexible Synthesis of Carbocyclic C-Nucleosides

0476449 - BFÚ 2018 RIV US eng J - Journal Article
Maier, L. - Khirsariya, P. - Hylse, O. - Adla, S.K. - Cernova, L. - Poljak, M. - Krajčovičová, S. - Weis, E. - Drápela, Stanislav - Souček, Karel - Paruch, K.
Diastereoselective Flexible Synthesis of Carbocyclic C-Nucleosides.
Journal of Organic Chemistry. Roč. 82, č. 7 (2017), s. 3382-3402. ISSN 0022-3263. E-ISSN 1520-6904
Institutional support: RVO:68081707
Keywords : mitsunobu * catalysis * alcohols
OECD category: Organic chemistry
Impact factor: 4.805, year: 2017

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.
Permanent Link: http://hdl.handle.net/11104/0272947