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Total Synthesis of (−)-Galanthamine by Remote Asymmetric Induction

Authors

  • Sumiaki Kodama,

    1. Department of Pharmaceutical Manufacturing Chemistry, Kyoto Pharmaceutical University, Misasagi, Yamashina, Kyoto 607-8414, Japan, Fax: (+81) 75-595-4775
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  • Yoshio Hamashima Dr.,

    1. Department of Pharmaceutical Manufacturing Chemistry, Kyoto Pharmaceutical University, Misasagi, Yamashina, Kyoto 607-8414, Japan, Fax: (+81) 75-595-4775
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  • Kiyoharu Nishide Prof. Dr.,

    1. Department of Pharmaceutical Manufacturing Chemistry, Kyoto Pharmaceutical University, Misasagi, Yamashina, Kyoto 607-8414, Japan, Fax: (+81) 75-595-4775
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  • Manabu Node Prof. Dr.

    1. Department of Pharmaceutical Manufacturing Chemistry, Kyoto Pharmaceutical University, Misasagi, Yamashina, Kyoto 607-8414, Japan, Fax: (+81) 75-595-4775
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Abstract

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Die entscheidende intramolekulare Michael-Addition zur Bildung des 5,7,5-Ringgerüsts von (−)-Galanthamin (1) gelang durch asymmetrische Ferninduktion eines von D-Phenylalanin abgeleiteten chiralen Imidazolidinon-Auxiliars (siehe Schema). Diese Totalsynthese von 1 verläuft im Unterschied zu früheren Synthesen nicht über das stark allergene Enon Narwedin.

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