One-Pot Synthesis of Structurally Diverse Iminosugar-Based Hybrid Molecules

A one-pot iminium-ion-based strategy has been developed for the synthesis of structurally novel iminosugar-based hybrid molecules. Iminiumion derived from l- rhamnose lactol- mesylatereacted with electron-rich aromatic systems in an inter/intra molecular fashion to furnish pyrrolidine-based iminosugarC-aryl glycosides with a high degree of stereoselectivity. Iminiumion also reacted readily with active methylene compounds such as 4-hydroxycoumarin, 4-hydroxyquinolinone, and lawsoneto provide iminosugarC-coumarin/quinolinone/naphthoquinonyl glycosides in very good yields. Azomethine ylidegenerated from an iminiumion derivative underwent dipolar cycloaddition reaction with 1,4-quinones to furnish novel isopyrrolonaphtho/anthroquinon-based iminosugar-hybrids. The preliminary cytotoxic activities of some of the synthesized iminosugar-hybrids have been assayed against various human cancer cell lines and some of the hybrid molecules exhibited promising anticancer activities.