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

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...

Full description

Saved in:
Bibliographic Details
Published inOrganic 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
LanguageEnglish
Published United States American Chemical Society 27.01.2023
Subjects
bioactive properties
glucosides
gramine
melatonin
Online AccessGet full text

Cover

More Information
Summary: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 of functional groups, as various indoles and thioglycosides are suitable. It also provides a reliable method for performing late-stage modifications of natural products, such as gramine and melatonin. Total syntheses of isatindigotindolosides I and II were successfully accomplished using the C2-thioglycosylation reaction as a key step.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:1523-7060
1523-7052
1523-7052
DOI:10.1021/acs.orglett.2c04270