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Synthesis 1994; 1994(3): 239-241
DOI: 10.1055/s-1994-25446
short paper
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Biomimetic Synthesis of Ascididemin and Derivatives

Gari Gellerman* , Amira Rudi, Yoel Kashman
  • *School of Chemistry, Tel Aviv University, Tel Aviv 69978, Israel
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Publication Date:
27 September 2002 (online)

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A two-step biomimetic synthesis of the pentacyclic pyrido[2,3,4-klacridine marine alkaloid ascididemin (3a) from quinolinequinone 5a and N-trifluoroacetamidokynuramine (4) is described. The crucial step (6 to 7) involves the simultaneous formation of two pyridine rings in a process which might well offer an explanation for the biogenetic synthesis in marine organisms. The preparation of substituted ascididemins by either starting from substituted quinoline-quinones, e.g., 5b to afford 11-methoxyascididemin (3b), or by nitration of 3a to the mono 1- or 3-nitroascididemins (8 and 9 respectively) is reported.