Synthesis of 1C-Aryl/Alkyl 2C-Branched Sugar-Fused Isochroman Derivatives by Sequential Prins and Friedel–Crafts Cyclizations on a Perlin Aldehyde Derived Substrate

Abstract

The synthesis of C-aryl/alkyl 2C-branched sugar-fused isochromans by using a carbohydrate-derived starting material is described. Our approach makes use of sequential Prins and Friedel–Crafts cyclizations in which a Perlin aldehyde derived homoallylic alcohol is converted into the target molecule. This strategy works well with many aldehydes and gives good yields with excellent selectivity.