D. Mujahidin, S. Doye
Jul 1, 2005
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Journal
European Journal of Organic Chemistry
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. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)