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An Efficient Route to Emodic Amine and Analogous O-Methyl Protected Derivatives Starting from Emodin

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Summary.

Emodic amine could be synthesized in a five-step approach in excellent overall yield by following a modified Curtius rearrangement strategy, starting from the naturally occurring emodin. This unique emodin derived 6-amino substituted polyhydroxylated anthraquinone may serve as a promising synthon for a new class of amino functionalized photodynamically active hypericin derivatives. In addition, the partially O-methyl protected 6-amino- and 6-carboxy-anthraquinones could be synthesized in high yields via selective O-methyl ether cleavage from the corresponding tri-O-methyl derivatives.

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Authors and Affiliations

  1. Institute of Organic Chemistry, Johannes Kepler University Linz, 4040, Linz, Austria

    Bernd Lackner, Klaus Bretterbauer & Heinz Falk

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  1. Bernd Lackner
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  2. Klaus Bretterbauer
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  3. Heinz Falk
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Correspondence to Heinz Falk.

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Lackner, B., Bretterbauer, K. & Falk, H. An Efficient Route to Emodic Amine and Analogous O-Methyl Protected Derivatives Starting from Emodin. Monatsh. Chem. 136, 1629–1639 (2005). https://doi.org/10.1007/s00706-005-0350-7

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  • DOI: https://doi.org/10.1007/s00706-005-0350-7

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