Back to the Sugars: A New Enantio and Diastereocontrolled Route to Hexoses from Furfural

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Abstract
An integrated enantio and diastereocontrolled route to both enantiomers of the eight possible hexoses has been explored starting from furfural, by employing the Sharpless asymmetric dihydroxylation as a key step. At the present, a route to six of the eight possible hexoses has been established. The present synthesis may be taken as a reversion of the sugar-originated furfural to the sugars via a levoglucosenone, a pyrolysate of cellulose, type intermediate.

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