Enantioselective Synthesis of (+)??(S)??Laudanosine and (–)??(S)??Xylopinine

D Mujahidin, S Doye

Index: Mujahidin, Didin; Doye, Sven European Journal of Organic Chemistry, 2005 , # 13 p. 2689 - 2693

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Citation Number: 41

Abstract

Abstract The study presents a new pathway for the enantioselective synthesis of benzylisoquinoline alkaloids. The key steps of the synthesis of (+)-(S)-laudanosine (1) and (– )-(S)-xylopinine (2) are a Sonogashira coupling that builds up the C1–C8a bond of the benzylisoquinoline skeleton, an intramolecular Ti-catalyzed hydroamination of an alkyne, and a subsequent enantioselective imine reduction according to Noyori's protocol.(© ...