Glycosyl Thiosulfonate: Stable Electrophilic Reagent for Synthesis of Thioglycosylated Indoles and Total Synthesis of Isatindigotindolosides

Zanjila Azeem; Sunny Maurya; Abhishek Kumar Gupta; Shalini Shalini; Ruchir Kant; Pintu Kumar Mandal

doi:10.1039/d5cc03279b

January 1, 2025Chemical Communications

Glycosyl Thiosulfonate: Stable Electrophilic Reagent for Synthesis of Thioglycosylated Indoles and Total Synthesis of Isatindigotindolosides

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Key Points

The study shows efficient synthesis of thioglycosylated indoles through glycosyl thiosulfonate.
This method utilizes copper-catalysis, leading to stable indole alkaloid frameworks.
Broad substrate scope indicates significant versatility in the synthesis process.
The use of glycosyl thiosulfonate as a reagent implies potential industrial applicability.

Implication

Copper-catalyzed thioglycosylation assembles indole alkaloids using stable glycosyl thiosulfonate, indicating a novel synthesis approach.

Abstract

We disclose a copper-catalyzed C2- or C3-thioglycosylation of indole with a shelf-stable and odorless glycosyl thiosulfonate to assemble indole alkaloid glucoside frameworks. This straightforward, catalytic system exhibits features of broad...

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Cite This Study

Azeem et al. (2025) studied this question.

synapsesocial.com/papers/68bb5f3e6d6d5674bcd035a4 https://doi.org/10.1039/d5cc03279b

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Glycosyl Thiosulfonate: Stable Electrophilic Reagent for Synthesis of Thioglycosylated Indoles and Total Synthesis of Isatindigotindolosides

Key Points

Implication

Abstract

Discussion

Cite This Study

Glycosyl Thiosulfonate: Stable Electrophilic Reagent for Synthesis of Thioglycosylated Indoles and Total Synthesis of Isatindigotindolosides

Key Points

Implication

Abstract

Discussion

Cite This Study

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