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Synthesis 1995; 1995(11): 1432-1444
DOI: 10.1055/s-1995-4112
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Radical Tandem Cyclizations by Anodic Decarboxylation of Carboxylic Acids

Agnes Matzeit, Hans J. Schäfer* , Christian Amatore
  • *Organisch-Chemisches Institut der Universität, Corrensstraße 40, D-48149 Münster, Germany, Fax +49 2 51 83 97 72
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Publication Date:
31 December 2000 (online)

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Radical tandem cyclizations are initiated by the Kolbe electrolysis of unsaturated carboxylic acids 4, 18, 23-25 which are prepared in a few steps. The efficiency of the radical tandem cyclization provides a short synthetic sequence to tricyclic products, e.g. angular triquinanes 7, 8, 11, 26-28. In this anodic tandem cyclization, three C-C bonds are formed regio-and stereoselectively in a one-pot reaction by intramolecular addition and intermolecular coupling. The use of different carboxylic acids as starting materials and various coacids gives versatile access to substituted tricyclic compounds.

tandem cyclization - anodic oxidation - angular triquinanes - simulation of product selectivity - Kolbe electrolysis - unsaturated carboxylic acids

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