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

Abstract

The acid-catalyzed reaction of D-mannitol 4 with bromoacetaldehyde diethyl acetal followed by periodate cleavage of the correspondmg diacetal 5 afforded (4S, 2R, S)-2-bromomethyl-4-hydroxymethyl-l, 3-dioxolane 3c in good yields, from which the title compound 1 is obtained by displacement of the bromine with lithium iodide. 0 1995 Wiley-Liss, Inc.