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Synlett 2017; 28(13): 1510-1516
DOI: 10.1055/s-0036-1589020
DOI: 10.1055/s-0036-1589020
synpacts
Glycosyl Stille Cross-Coupling with Anomeric Nucleophiles – A General Solution to a Long-Standing Problem of Stereocontrolled Synthesis of C-Glycosides
Further Information
Publication History
Received: 10 March 2017
Accepted after revision: 06 April 2017
Publication Date:
24 May 2017 (online)
Abstract
Aryl C-glycosides are common structural motifs found in bioactive natural products and commercially available drugs. Despite their importance, most chemical methods to prepare C-glycosides have relied on the nucleophilic addition/substitution of a glycosyl electrophile, which result in variable anomeric selectivities and yields. Furthermore, these methods are not compatible with saccharides containing free hydroxyl groups. Here, we describe a direct cross-coupling reaction of anomeric nucleophiles (anomeric stannanes) and aryl halides. This method is the first general approach to the synthesis of aryl C-glycosides resulting in exclusive anomeric selectivities for both anomers for a broad range of aryl and carbohydrate coupling partners (including unprotected saccharides).
1 Introduction
2 Synthesis of Anomeric Stannanes
3 Glycosyl Stille Cross-Coupling
4 Future Outlook
5 Summary
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