Collect. Czech. Chem. Commun. 1993, 58, 2517-2522

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

Martin Mandela, Tomáš Hudlickýa, Lawrence D. Kwartb and Gregg M. Whitedb

a Virginia Polytechnic Institute and State University, Blacksburg, VA 24061, U.S.A.
b Genencor International, Inc., South San Francisco, CA 94080, U.S.A.


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.