Ugi-type four-component reaction for a novel synthesis of 5-oxo-perhydrofuro[3,2-b]pyran carboxylate derivatives

The four-component coupling (4CC) of sugar hydroxyaldehyde, Meldrum's acid, isocyanide, and a secondary alcohol in dichloromethane has been accomplished at room temperature in a highly stereoselective manner to produce a novel class of carbohydrate derivatives, 5-oxo-perhydrofuro[3,2-b]pyrans in good yields with trans-selectivity. The stereochemistry of the products was assigned by various NMR experiments. (C) 2010 Elsevier Ltd. All rights reserved.