Synthesis of Methylene Tetrahydrofurane‐Fused Carbohydrates

Abstract

AbstractA reliable method is disclosed to introduce a fused methylene tetrahydrofuran ring into carbohydrates. The resulting bicyclic saccharides can be used as scaffolds in medicinal chemistry and drug design. In addition, the enol ether functionality serves as a handle that enables modification in biological systems via photoclick chemistry. The approach is based on the regioselective oxidation of the C‐3 hydroxy group in gluco‐configured pyranosides, followed by stereoselective indium‐mediated allylation. The ring formation is induced by an iodocyclization reaction with a neighboring hydroxy group. Subsequent dehydrohalogenation affords the desired methylene‐tetrahydrofuran‐containing carbohydrates.