Copper-Catalyzed Intramolecular Alkoxylation of Purine Nucleosides: One-Step Synthesis of 5′‑O,8-Cyclopurine Nucleosides

Copper-Catalyzed Intramolecular Alkoxylation of Purine Nucleosides: One-Step Synthesis of 5′‑O,8-Cyclopurine Nucleosides

A novel copper-catalyzed intramolecular dehydrogenative alkoxylation of purine nucleosides has been developed successfully, providing the 5′-O,8-cyclopurine nucleosides in one-step with a yield up to 90%. The method, which utilized an inexpensive CuCl catalyst and a di-tert-butyl peroxide (DTBP) oxi...

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Veröffentlicht in:Journal of organic chemistry 2015-10, Vol.80 (19), p.9446-9453
Hauptverfasser: Yu, Mingwu, Wang, Zhiqian, Hu, Junbin, Li, Shunlai, Du, Hongguang
Format: Artikel
Sprache:eng
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Zusammenfassung:A novel copper-catalyzed intramolecular dehydrogenative alkoxylation of purine nucleosides has been developed successfully, providing the 5′-O,8-cyclopurine nucleosides in one-step with a yield up to 90%. The method, which utilized an inexpensive CuCl catalyst and a di-tert-butyl peroxide (DTBP) oxidant was suitable in a broad substrate scope and proceeded well even in gram scale.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.5b01360