| MAIER, Lukáš, PrashantKumar KHIRSARIYA, Ondřej HYLSE, Santosh Kumar ADLA, Lenka ČERNOVÁ, Michal POLJAK, Soňa KRAJČOVIČOVÁ, Erik WEIS, Stanislav DRÁPELA, Karel SOUČEK a Kamil PARUCH. Diastereoselective Flexible Synthesis of Carbocyclic C Nucleosides. The Journal of Organic Chemistry. WASHINGTON, DC USA: American Chemical Society, 2017, roč. 82, č. 7, s. 3382-3402. ISSN 0022-3263. Dostupné z: 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 a Kamil PARUCH. Diastereoselective Flexible Synthesis of Carbocyclic C Nucleosides. \textit{The Journal of Organic Chemistry}. WASHINGTON, DC USA: American Chemical Society, 2017, roč.~82, č.~7, s.~3382-3402. ISSN~0022-3263. Dostupné z: https://dx.doi.org/10.1021/acs.joc.6b02594.
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