Diastereoselective Flexible Synthesis of Carbocyclic C Nucleosides

Varování

Publikace nespadá pod Ekonomicko-správní fakultu, ale pod Přírodovědeckou fakultu. Oficiální stránka publikace je na webu muni.cz.

Autoři	MAIER Lukáš KHIRSARIYA PrashantKumar HYLSE Ondřej ADLA Santosh Kumar ČERNOVÁ Lenka POLJAK Michal KRAJČOVIČOVÁ Soňa WEIS Erik DRÁPELA Stanislav SOUČEK Karel PARUCH Kamil
Rok publikování	2017
Druh	Článek v odborném periodiku
Časopis / Zdroj	The Journal of Organic Chemistry
Fakulta / Pracoviště MU	Přírodovědecká fakulta
Citace
www	přístup k publikaci
Doi	http://dx.doi.org/10.1021/acs.joc.6b02594
Obor	Organická chemie
Klíčová slova	POLYHYDROXYLATED N-ALKOXYPIPERIDINES; CHEMICAL-STABILITY; ANTITUMOR-ACTIVITY; ANALOGS; DERIVATIVES; MITSUNOBU; CATALYSIS; ALCOHOLS
Popis	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.
Související projekty:	Czech Infrastructure for Integrative Structural Biology CZ-OPENSCREEN: National Infrastructure for Chemical Biology