Stereochemical versatillity in synthesis of substituted cycloalkanes from acyclic unsaturated sugars

Abstract

Acyclic unsaturated sugars obtained by Wittig extension of aldehydo arabinose precursors undergo stereoselective Diels–Alder addition of cyclopentadiene, permitting isolation of a single, crystalline, opticallly pure norbornene adduct whose stereochemistry may be controlled by the enantiomeric form of the sugar used and the conditions of the cycloaddition reaction.