Diastereoselective Synthesis of the Aporphine Alkaloid (+)-Cataline. Hydroxylation with Vanadium(V) Trifluoride Oxide

Authors

  • Dr. Johannes Hartenstein,

    Corresponding author
    1. Gödecke Forschungsinstitut, Chemische Forschung und Entwicklung, Postfach 5 69, D-7800 Freiburg (Germany)
    • Gödecke Forschungsinstitut, Chemische Forschung und Entwicklung, Postfach 5 69, D-7800 Freiburg (Germany)
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  • Dr. Gerhard Satzinger

    1. Gödecke Forschungsinstitut, Chemische Forschung und Entwicklung, Postfach 5 69, D-7800 Freiburg (Germany)
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  • We thank G. Pohlmann for careful experimental assistance.

Abstract

original image

Simplicity and stereospecificity characterize a one-step synthesis of (±)-cataline (3) from (±)-laudanosine (1) (R[DOUBLE BOND]CH3O, R′[DOUBLE BOND]CH3). The product is accompanied by small amounts of (±)-glaucine (2).

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