Asymmetric synthesis of (R)-reticuline. A new strategy for the asymmetric synthesis of isoquinolines via enantioselective epoxidation or dihydroxylation |
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Authors: | Rolf Hirsenkorn |
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Institution: | aConsortium fu¨r elektrochemische Industrie GmbH, Zielstattstr. 20, D-8000 Mu¨nchen 70,FRG, eine Geselischaft der Wacker-Chemie GmbH |
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Abstract: | A new strategy for the asymmetric synthesis of 1-benzyl-1,2,3,4-tetrahydroisoquinolines7 ? 9 has been developed. The route involves introduction of asymmetry via enantioselective epoxidation or dihydroxylafion 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. |
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