From Chlorobenzene to a Carbohydrate in Two Steps. A New Chemoenzymatic Synthesis of 2,3-O-Isopropylidene-D-erythruronolactone

Controlled oxidation of chloroepoxide V with two equivalents of sodium periodate furnished 2,3-O-isopropylidene-D-erythruronolactone (I) in 63% yield. This procedure was augmented by combining the protection of diol III, the oxidation of acetonide IV to V, and the subsequent oxidative cleavage to I into one operation which yielded, on medium scale, the title lactone in 51% yield. detailed procedure of preparation and physical constants are provided for lactone I.