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Pericyclic Reactions in Nature: Spontaneous Cope Rearrangement Inactivates Algae Pheromones

Authors

  • Prof. Dr. Wilhelm Boland,

    Corresponding author
    1. Institut für Organische Chemie und Biochemie der Universität, Gerhard-Domagk-Strasse 1, D- 53121 Bonn (Germany) Telefax: Int. code + (228) 735388
    • Institut für Organische Chemie und Biochemie der Universität, Gerhard-Domagk-Strasse 1, D- 53121 Bonn (Germany) Telefax: Int. code + (228) 735388
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  • Dipl.-Chem. Georg Pohnert,

    1. Institut für Organische Chemie und Biochemie der Universität, Gerhard-Domagk-Strasse 1, D- 53121 Bonn (Germany) Telefax: Int. code + (228) 735388
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  • Dr. Ingo Maier

    1. Fakultät für Biologie der Universität Konstanz (Germany)
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  • Biosynthesis of Algae Pheromones, Part 4. This work was supported by the Deutsche Forschungsgemeinschaft and the Fonds der Chemischen Industrie. We thank Prof. Dr. D. G. Müller (Universität Konstanz) for his support. Part 3: ref. [17].

  • Dedicated to Professor Hans-Jürgen Bestmann on the occasion of his 70th birthday

Abstract

original image

A pheromone roughly 100 times more effective than cyclohepta-1,4-diene 2 (R = C2H5, ectocarpene) is its biosynthetic precursor 1. This thermally labile cis-disubstituted cyclopropane is the actual signaling agent of the marine brown algae Ectocarpus siliculosus. The [3,3]sigmatropic rearrangement of 1 giving 2 (t1/2 = 21 min at 18°C) is the fastest known reaction for the spontaneous inactivation of a pheromone.

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