Diastereoselective Flexible Synthesis of Carbocyclic C Nucleosides

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Authors

MAIER Lukáš KHIRSARIYA PrashantKumar HYLSE Ondřej ADLA Santosh Kumar ČERNOVÁ Lenka POLJAK Michal KRAJČOVIČOVÁ Soňa WEIS Erik DRÁPELA Stanislav SOUČEK Karel PARUCH Kamil

Year of publication 2017
Type Article in Periodical
Magazine / Source The Journal of Organic Chemistry
MU Faculty or unit

Faculty of Science

Citation
Web přístup k publikaci
Doi http://dx.doi.org/10.1021/acs.joc.6b02594
Field Organic chemistry
Keywords POLYHYDROXYLATED N-ALKOXYPIPERIDINES; CHEMICAL-STABILITY; ANTITUMOR-ACTIVITY; ANALOGS; DERIVATIVES; MITSUNOBU; CATALYSIS; ALCOHOLS
Description 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.
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