We developed an efficient synthetic route for functionalized aryl-β-C-glycosides, which are difficult to prepare by conventional methods. An aryl halide having an ester, cyano, or carbonyl group was treated with 2,4,6-triisopropylphenyllithium in the presence of a δ-lactone (Barbier-type reaction conditions) to afford a coupling product. The following deoxygenation gave the desired aryl-β-C-glycoside in good yield.
- 2 4 6-Triisopropylphenyllithium
- Barbier-type reaction
- Halogen-metal exchange reaction
ASJC Scopus subject areas
- Drug Discovery
- Organic Chemistry