Synthesis ofC-acyl furanosidesviathe cross-coupling of glycosyl esters with carboxylic acids

Yongliang Wei, Jenny Lam, Tianning Diao

Research output: Contribution to journalArticlepeer-review


C-Acyl furanosides are versatile synthetic precursors to a variety of natural products, nucleoside analogues, and pharmaceutical molecules. This report addresses the unmet challenge in preparingC-acyl furanosides by developing a cross-coupling reaction between glycosyl esters and carboxylic acids. A key step is the photoredox activation of the glycosyl ester, which promotes the homolysis of the strong anomeric C-O bond through CO2evolution to afford glycosyl radicals. This method embraces a large scope of furanoses, pyranoses, and carboxylic acids, and is readily applicable to the synthesis of a thymidine analogue and diplobifuranylone B, as well as the late-stage modification of (+)-sclareolide. The convenient preparation of the redox active glycosyl ester from native sugars and the compatibility with common furanoses exemplifies the potential of this method in medicinal chemistry.

Original languageEnglish (US)
Pages (from-to)11414-11419
Number of pages6
JournalChemical Science
Issue number34
StatePublished - Sep 14 2021

ASJC Scopus subject areas

  • General Chemistry


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