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Synfacts 2009(5): 0477-0477
DOI: 10.1055/s-0028-1088168
DOI: 10.1055/s-0028-1088168
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag
Stuttgart ˙ New York
Synthesis of Berkelic Acid Methyl Ester
P. Buchgraber, T. N. Snaddon, C. Wirtz, R. Mynott, R. Goddard, A. Fürstner*
Max-Planck-Institut für Kohlenforschung, Mülheim an der Ruhr, Germany
Weitere Informationen
Publikationsverlauf
Publikationsdatum:
22. April 2009 (online)

Significance
Berkelic acid was isolated from a Penicillium species, native to a highly acidic (pH 2.5) and heavy-metal salt-rich flooded former copper mine. This metabolite showed promising activity against an ovarian cancer cell line. The relative configuration was originally assigned based on NMR experiments. Herein, the first total synthesis is described leading to a revision of the proposed structure which is epimeric at C9, C15, and C17.