Stereoselective Synthesis of C-Aryl-α-Glycosides by Reductive C(sp2)–C(sp3) Cross-Coupling Reaction

Author:

Kudo Noyuri1,Chiba Suzuka1,Usui Kazuteru,Hirai Go1ORCID,Ono Shunsuke1,Nagatoishi Masataka1,Yoritate Makoto1,Karasawa Satoru2

Affiliation:

1. Graduate School of Pharmaceutical Sciences, Kyushu University

2. Showa Pharmaceutical University

Abstract

Abstract C-Aryl glycosides have attracted considerable interest as biologically active natural products and as O-aryl glycoside mimetics in drug discovery. Here, we describe a straightforward synthesis of C-aryl glycosides by photoredox/Ni dual-catalyzed reductive cross-coupling between glycosyl bromides and aryl bromides. This methodology enables a highly α-stereoselective synthesis of C-aryl glucosides, galactosides, and mannosides.

Funder

Japan Society for the Promotion of Science

Leading Pioneers Science Foundation

Asian Chemical Biology Initiative

Japan Agency for Medical Research and Development

Mizutani Foundation for Glycoscience

Ministry of Education, Culture, Sports, Science and Technology

Publisher

Georg Thieme Verlag KG

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