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

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 sy...

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Bibliographic Details
Published in:Organic & biomolecular chemistry 2020-07, Vol.18 (27), p.5095-5109
Main Authors: Xu, Lin-Yi, Fan, Nai-Li, Hu, Xiang-Guo
Format: Article
Language:English
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Summary: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.
ISSN:1477-0520
1477-0539
DOI:10.1039/d0ob00711k