Simple Stereoselective Synthesis of Eburnamonine

Authors

  • Friederike Klatte,

    Corresponding author
    1. Organisch-chemisches Institut der Technischen Universität, Schneiderberg 1 B, D-3000 Hannover 1 (Germany)
    • Organisch-chemisches Institut der Technischen Universität, Schneiderberg 1 B, D-3000 Hannover 1 (Germany)
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  • Dipl.-Chem. Ulrich Rosentreter,

    1. Organisch-chemisches Institut der Technischen Universität, Schneiderberg 1 B, D-3000 Hannover 1 (Germany)
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  • Prof. Dr. Ekkehard Winterfeldt

    1. Organisch-chemisches Institut der Technischen Universität, Schneiderberg 1 B, D-3000 Hannover 1 (Germany)
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  • Reactions of Indole Derivatives, Part 36. This work was supported by the Deutsche Forschungsgemeinschaft and the Fonds der Chemischen Industrie (U. R. thanks the Fonds der Chemischen Industrie for a Promotionsstipendium).—Part 35: J. Müller, E. Winterfeldt, Chem. Ber., in the press.

Abstract

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Regioselective ring opening of the cyclopropane derivative(1), R[DOUBLE BOND]C2H5, is the key step in the synthesis of the vincamine alkaloid eburnamonine (2). The cis-D,C linkage in (2) represents the crucial stereochemical problem in this series.

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