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Synlett 1995; 1995(9): 981-983
DOI: 10.1055/s-1995-5121
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Transition Metal-Diene Complexes in Organic Synthesis, Part 24.9b Total Synthesis of the Naturally Occurring Free Radical Scavenger Carazostatin

Hans-Joachim Knölker* , Thomas Hopfmann
  • *Institut für Organische Chemie, Universität Karlsruhe, Richard-Willstätter-Allee, D-76131 Karlsruhe, Germany, Fax +49(721)698529; E-mail knoe@ochhades.chemie.uni-karlsruhe.de
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Publication Date:
31 December 2000 (online)

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A consecutive iron-mediated C-C and C-N bond formation has been utilized for a short and high overall yield synthesis of the free radical scavenger carazostatin. The key steps are electrophilic aromatic substitution of an appropriately substituted arylamine by the iron-coordinated cyclohexadienylium cation, iron-mediated quinone imine cyclization, and demetalation to the 3-hydroxycarbazole.

free radical scavenger - carazostatin - carbazole alkaloids - tricarbonyliron-diene complexes - quinone imine cyclization