Copper-Catalyzed C2- or C3-Thioglycosylation of Indoles with N‑(Thioglycosides)succinimides: An Effective Strategy for the Total Synthesis of Isatindigotindolosides

• Published in: Organic letters Vol. 25; no. 3; pp. 528 - 532
• Main Authors: Huang, Jie, Sun, Wen-Wu, Li, Jin-Quan, Ma, Ao-Di, Liu, Ji-Kai, Wu, Bin
• Format: Journal Article
• Language: English
• Published: United States American Chemical Society 27.01.2023
• Subjects: bioactive properties; glucosides; gramine; melatonin

Isatindigotindolosides, indoles containing a 1-S-β-glucopyranosyl unit at position C2, show promising bioactivity. Here, we report a copper-catalyzed C2- or C3-thioglycosylation of indoles with N-(thioglycosides)­succinimides to construct indole alkaloid glucosides. This reaction is widely tolerant...