Iodine-catalyzed etherification of morroniside

In this study, we describe a highly selective etherification procedure of unprotected morroniside catalyzed by molecular iodine in acetone. The etherification reaction furnished 7-O-alkyl ether derivatives in reasonable yields within few hours under neutral conditions. Studies of the obtained products on cytotoxicity activity in colon 26- L5 cell line were examined. Among the tested compounds, 7-O-dodecylmorroniside showed moderate cytotoxic activity, having IC50 values equal to 20.9 μM. © 2009 Pharmaceutical Society of Japan.