Chemoselective and Diastereoselective Synthesis of C-Aryl Nucleoside Analogues by Nickel-Catalyzed Cross-Coupling of Furanosyl Acetates with Aryl Iodides
Yuxi Li
Tsinghua Institute of Multidisciplinary Biomedical Research, Tsinghua University, Beijing, 100084 China
National Institute of Biological Sciences, Beijing, 102206 China
Search for more papers by this authorZheng Wang
National Institute of Biological Sciences, Beijing, 102206 China
These authors contributed equally to this work.
Search for more papers by this authorLuyang Li
National Institute of Biological Sciences, Beijing, 102206 China
These authors contributed equally to this work.
Search for more papers by this authorXiaoying Tian
National Institute of Biological Sciences, Beijing, 102206 China
Graduate School of Peking Union Medical College and Chinese Academy of Medical Sciences, Beijing, 102206 China
Search for more papers by this authorDr. Feng Shao
Tsinghua Institute of Multidisciplinary Biomedical Research, Tsinghua University, Beijing, 100084 China
National Institute of Biological Sciences, Beijing, 102206 China
Graduate School of Peking Union Medical College and Chinese Academy of Medical Sciences, Beijing, 102206 China
Search for more papers by this authorCorresponding Author
Dr. Chao Li
Tsinghua Institute of Multidisciplinary Biomedical Research, Tsinghua University, Beijing, 100084 China
National Institute of Biological Sciences, Beijing, 102206 China
Graduate School of Peking Union Medical College and Chinese Academy of Medical Sciences, Beijing, 102206 China
Search for more papers by this authorYuxi Li
Tsinghua Institute of Multidisciplinary Biomedical Research, Tsinghua University, Beijing, 100084 China
National Institute of Biological Sciences, Beijing, 102206 China
Search for more papers by this authorZheng Wang
National Institute of Biological Sciences, Beijing, 102206 China
These authors contributed equally to this work.
Search for more papers by this authorLuyang Li
National Institute of Biological Sciences, Beijing, 102206 China
These authors contributed equally to this work.
Search for more papers by this authorXiaoying Tian
National Institute of Biological Sciences, Beijing, 102206 China
Graduate School of Peking Union Medical College and Chinese Academy of Medical Sciences, Beijing, 102206 China
Search for more papers by this authorDr. Feng Shao
Tsinghua Institute of Multidisciplinary Biomedical Research, Tsinghua University, Beijing, 100084 China
National Institute of Biological Sciences, Beijing, 102206 China
Graduate School of Peking Union Medical College and Chinese Academy of Medical Sciences, Beijing, 102206 China
Search for more papers by this authorCorresponding Author
Dr. Chao Li
Tsinghua Institute of Multidisciplinary Biomedical Research, Tsinghua University, Beijing, 100084 China
National Institute of Biological Sciences, Beijing, 102206 China
Graduate School of Peking Union Medical College and Chinese Academy of Medical Sciences, Beijing, 102206 China
Search for more papers by this authorAbstract
Canonical nucleosides are vulnerable to enzymatic and chemical degradation, yet their stable mimics—C-aryl nucleosides—have demonstrated potential utility in medicinal chemistry, chemical biology, and synthetic biology, although current synthetic methods remain limited in terms of scope and selectivity. Herein, we report a cross-electrophile coupling to prepare C-aryl nucleoside analogues from readily available furanosyl acetates and aryl iodides. This nickel-catalyzed modular approach is characterized by mild reaction conditions, broad substrate scope, excellent β-selectivity, and high functional-group compatibility. The exclusive chemoselectivity with respect to the aryl iodide enables efficient preparation of a variety of C-aryl halide furanosides suitable for various downstream transformations. The practicality of this transformation is demonstrated through the synthesis of a potent analogue of a naturally occurring NF-κB activator.
Conflict of interest
The authors declare no conflict of interest.
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