Issue 27, 2020

Recent development in the synthesis of C-glycosides involving glycosyl radicals

Abstract

C-Glycosylation involving glycosyl radical intermediates is a particularly effective approach to access C-glycosides, which are core units of a great number of natural products, bioactive compounds and marketed drugs. In this review, we summarize the progress of glycosyl radical-based C-glycoside synthesis between 1999–2020, focusing on the stereoselectivity and recently developed methodologies such as α-alkoxyacyl telluride-related, photo-mediated and transition-metal catalysed reactions. Metal-mediated reductive cross coupling is also covered due to its close relationship with the latter approaches. To introduce several strategies for achieving uncommon β-stereoselective C-glycosylation, we also briefly described organotin-based methods.

Graphical abstract: Recent development in the synthesis of C-glycosides involving glycosyl radicals

Article information

Article type
Review Article
Submitted
04 Apr. 2020
Accepted
09 Jūn. 2020
First published
10 Jūn. 2020

Org. Biomol. Chem., 2020,18, 5095-5109

Recent development in the synthesis of C-glycosides involving glycosyl radicals

L. Xu, N. Fan and X. Hu, Org. Biomol. Chem., 2020, 18, 5095 DOI: 10.1039/D0OB00711K

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