Syntheses of four d- and l-hexoses via diastereoselective and enantioselective dihydroxylation reactions

Abstract

An expeditious approach to various protected hexoses has been developed by the use of the Sharpless catalytic asymmetric dihydroxylation reaction. Applying the Sharpless catalytic asymmetric dihydroxylation reaction on vinylfuran, diols with high enantioexcess are produced. The resulting diols can be stereoselectively transformed into either protected d- or l-mannose in five steps and approximately 39% yield from furfural. Similarly, both d- and l-talose and gulose have been synthesized in 19% overall yields, respectively. Using a modified strategy, both protected d- and l-gulo- and allo-sugar-δ-lactones were synthesized in eight steps and ∼20% overall yield from furfural.