Biosynthetic Origin of the Oxygen Atoms of Tetracenomycin C

Authors

  • Dipl.-Ing. Györgyi Udvarnoki,

    1. Institut für Organische Chemie der Universität, Tammannstrasse 2, D-37077 Göttingen (Germany). Telefax: Int. code + (551)39-9660
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  • Dr. Christina Wagner,

    1. Hans-Knöll-Institut für Naturstoff-Forschung e.V
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  • Dipl.-Chem. Reinhard Machinek,

    1. Institut für Organische Chemie der Universität, Tammannstrasse 2, D-37077 Göttingen (Germany). Telefax: Int. code + (551)39-9660
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  • Priv.-Doz. Dr. Jürgen Rohr

    Corresponding author
    1. Institut für Organische Chemie der Universität, Tammannstrasse 2, D-37077 Göttingen (Germany). Telefax: Int. code + (551)39-9660
    • Institut für Organische Chemie der Universität, Tammannstrasse 2, D-37077 Göttingen (Germany). Telefax: Int. code + (551)39-9660
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  • This work was supported by the Deutsche Forschungsgemeinschaft, the Bundesministerium für Forschung und Technologie, and the Fonds der Chemischen Industrie.

  • Dedicated to Professor Wolfgang Lüttke on the occasion of his 75th birthday

Abstract

original image

Water and not acetate is the source of the oxygen atom 4a-OH in the biosynthesis of tetracenomycin C. Based on this unusual finding, an intermediate epoxide is postulated, which has to be “cis opened” to attain the required stereochemistry at C-4a and C-12a (see reaction sequence below).

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