A Cascade of Prins Reaction and Pinacol‐Type Rearrangement: Access to 2,3‐Dideoxy‐3C‐Formyl β‐C‐Aryl/Alkyl Furanosides and 2‐Deoxy‐2C‐Branched β‐C‐Aryl Furanoside

Abstract

2,3‐Dideoxy‐3C‐formyl β‐C‐aryl/alkyl furanosides were synthesized in a stereoselective manner through a cascade of Prins reaction and pinacol‐type rearrangement of an –OTBDPS protected homoallylic alcohol, derived from d‐mannitol, and various carbonyl compounds. Furthermore, this method was successfully applied to the synthesis of a fused‐bicyclic β‐C‐aryl furanoside moiety and a 2,3‐dideoxy‐3C‐methyl β‐C‐aryl furanoside which are found in core structures of bioactive molecules. Further, the strategy was extended to a silyl‐Prins reaction for the synthesis of a 2‐deoxy‐2C‐branched β‐C‐aryl furanoside.