Novel and stereoselective asymmetric synthesis of an amino sugar analogue, furanodictine A

A novel and efficient strategy is described for the asymmetric synthesis of the first 3,6-anhydrosugar to be isolated from natural sources, furanodictine A. The synthetic process is based on requisite stereodefined manipulation of the functionalized amino alcohol obtained through nucleophilic addition of vinyl Grignard reagent to the aminal incorporating the d-arabinofuranose-derived skeleton in a complete stereoselective manner.