ASYMMETRIC SYNTHESIS OF (R)-RETICULINE - A NEW STRATEGY FOR THE ASYMMETRIC SYNTHESIS OF ISOQUINOLINES VIA ENANTIOSELECTIVE EPOXIDATION OR DIHYDROXYLATION

Article abstract of DOI:10.1016/S0040-4039(00)97306-4

A new strategy for the asymmetric synthesis of 1-benzyl-1,2,3,4-tetrahydroisoquinolines 7 - 9 has been developed.The route involves introduction of asymmetry via enantioselective epoxidation or dihydroxylation of corresponding stilbene precursors followed by aminolysis and Pomeranz-Fritsch cyclization.The strategy has been successfully applied to the asymmetric synthesis of (R)-reticuline (9), the key intermediate in the synthesis of morphine alkaloids on the biomimetic route.