MAIER, Lukáš, PrashantKumar KHIRSARIYA, Ondřej HYLSE, Santosh Kumar ADLA, Lenka ČERNOVÁ, Michal POLJAK, Soňa KRAJČOVIČOVÁ, Erik WEIS, Stanislav DRÁPELA, Karel SOUČEK and Kamil PARUCH. Diastereoselective Flexible Synthesis of Carbocyclic C Nucleosides. The Journal of Organic Chemistry. WASHINGTON, DC USA: American Chemical Society, 2017, vol. 82, No 7, p. 3382-3402. ISSN 0022-3263. Available from: https://dx.doi.org/10.1021/acs.joc.6b02594. |
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@article{1382487, author = {Maier, Lukáš and Khirsariya, PrashantKumar and Hylse, Ondřej and Adla, Santosh Kumar and Černová, Lenka and Poljak, Michal and Krajčovičová, Soňa and Weis, Erik and Drápela, Stanislav and Souček, Karel and Paruch, Kamil}, article_location = {WASHINGTON, DC USA}, article_number = {7}, doi = {http://dx.doi.org/10.1021/acs.joc.6b02594}, keywords = {POLYHYDROXYLATED N-ALKOXYPIPERIDINES; CHEMICAL-STABILITY; ANTITUMOR-ACTIVITY; ANALOGS; DERIVATIVES; MITSUNOBU; CATALYSIS; ALCOHOLS}, language = {eng}, issn = {0022-3263}, journal = {The Journal of Organic Chemistry}, title = {Diastereoselective Flexible Synthesis of Carbocyclic C Nucleosides}, url = {http://pubs.acs.org/doi/abs/10.1021/acs.joc.6b02594}, volume = {82}, year = {2017} }
TY - JOUR ID - 1382487 AU - Maier, Lukáš - Khirsariya, PrashantKumar - Hylse, Ondřej - Adla, Santosh Kumar - Černová, Lenka - Poljak, Michal - Krajčovičová, Soňa - Weis, Erik - Drápela, Stanislav - Souček, Karel - Paruch, Kamil PY - 2017 TI - Diastereoselective Flexible Synthesis of Carbocyclic C Nucleosides JF - The Journal of Organic Chemistry VL - 82 IS - 7 SP - 3382-3402 EP - 3382-3402 PB - American Chemical Society SN - 00223263 KW - POLYHYDROXYLATED N-ALKOXYPIPERIDINES KW - CHEMICAL-STABILITY KW - ANTITUMOR-ACTIVITY KW - ANALOGS KW - DERIVATIVES KW - MITSUNOBU KW - CATALYSIS KW - ALCOHOLS UR - http://pubs.acs.org/doi/abs/10.1021/acs.joc.6b02594 L2 - http://pubs.acs.org/doi/abs/10.1021/acs.joc.6b02594 N2 - 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. ER -
MAIER, Lukáš, PrashantKumar KHIRSARIYA, Ondřej HYLSE, Santosh Kumar ADLA, Lenka ČERNOVÁ, Michal POLJAK, Soňa KRAJČOVIČOVÁ, Erik WEIS, Stanislav DRÁPELA, Karel SOUČEK and Kamil PARUCH. Diastereoselective Flexible Synthesis of Carbocyclic C Nucleosides. \textit{The Journal of Organic Chemistry}. WASHINGTON, DC USA: American Chemical Society, 2017, vol.~82, No~7, p.~3382-3402. ISSN~0022-3263. Available from: https://dx.doi.org/10.1021/acs.joc.6b02594.
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