Open AccessSynthesis of C6-Substituted Purine Nucleoside Analogues via Late-Stage Photoredox/Nickel Dual Catalytic Cross-Coupling
Author(s) -
James J. Perkins,
Valerie W. Shurtleff,
Alayna Johnson,
Abdellatif El Marrouni
Publication year - 2021
Publication title -
acs medicinal chemistry letters
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.065
H-Index - 66
ISSN - 1948-5875
DOI - 10.1021/acsmedchemlett.0c00673
Subject(s) - nucleoside , purine , combinatorial chemistry , nickel , drug discovery , chemistry , catalysis , coupling (piping) , alkyl , coupling reaction , organic chemistry , stereochemistry , materials science , biochemistry , enzyme , metallurgy
Nucleoside analogues have been and continue to be extremely important compounds in drug discovery. Despite the significant effort dedicated to their synthesis, medicinal chemistry campaigns around these structures are often hampered by synthetic challenges. We describe a strategy for the functionalization of purine nucleosides via photoredox and nickel-catalyzed sp 2 -sp 3 cross-coupling. The conditions described herein allow for coupling of unprotected nucleosides with readily available alkyl bromides, providing opportunities for their application to parallel medicinal chemistry.