Synthesis of one diastereomeric couple of the mucolytic drug domiodol [(4S,2R,S)-2-iodomethyl-4-hydroxymethyl-1,3-dioxolane] from D-mannitol as chiral starting material

The acid-catalyzed reaction of D-mannitol 4 with bromoacetaldehyde diethyl acetal followed by periodate cleavage of the corresponding diacetal 5 afforded (4S,2R, S)-2-bromomethyl-4-hydroxymethyl-1,3-dioxolane 3c in good yields, from which the title compound 1 is obtained by displacement of the bromine with lithium iodide. (C) 1995 Wiley-Liss, Inc.