Efficient Synthesis of Carbohydrate-containing Carbocyclic Compounds Based on Palladium-catalyzed Vinylation of Sugars and Subsequent Diels-Alder Reaction

摘要

In the presence of catalytic amount of Pd(dba)_2 and P(o-tol)_3, the reaction of 3,4,6-tri-O-acetyl-2-bromo-D-glucal with ethylene proceeded smoothly to afford the conjugated dieno-pyranoside in high yield. The Diels-Alder reaction of this carbohydrate-derived diene with some dienophiles constructed chiral carbocyclic system.