Stereoselective synthesis of hexahydrofuro[3,4-b]furan-4-ol and its dimer via tandem Prins and pinacol rearrangement

Abstract

A novel synthetic route for the cyclization of ((4S,5R)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl)methanol with aldehydes to give hexahydrofuro[3,4-b]furan-4-ol and its dimer was developed. A variety of substituted furanol (up to 86%) and its bis-derivatives were obtained in good yields (up to 66%) with excellent diastereo- and enantio-selectivity mediated by borontrifluoride etherate. The dimer was conveniently converted into its corresponding monomer using aqueous zinc(II) chloride in THF in quantitative yields.