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Synfacts 2009(5): 0477-0477  
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

Contributor(s): Philip Kocienski, Arndt W. Schmidt
P. Buchgraber, T. N. Snaddon, C. Wirtz, R. Mynott, R. Goddard, A. Fürstner*
Max-Planck-Institut für Kohlenforschung, Mülheim an der Ruhr, Germany
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Publikationsdatum:
22. April 2009 (online)

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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.