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A Synthesis-Driven Structure Revision of Berkelic Acid Methyl Ester

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Buchgraber,  Philipp
Research Department Fürstner, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Snaddon,  Thomas N.
Research Department Fürstner, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Wirtz,  Cornelia
Service Department Mynott (NMR), Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Mynott,  Richard
Service Department Mynott (NMR), Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Goddard,  Richard
Service Department Lehmann (EMR), Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Fürstner,  Alois
Research Department Fürstner, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Citation

Buchgraber, P., Snaddon, T. N., Wirtz, C., Mynott, R., Goddard, R., & Fürstner, A. (2008). A Synthesis-Driven Structure Revision of Berkelic Acid Methyl Ester. Angewandte Chemie International Edition, 47(44), 8450-8454. doi:10.1002/anie.200803339.


Cite as: http://hdl.handle.net/11858/00-001M-0000-0024-B3C7-3
Abstract
A subtle difference: A single step suffices to transform a linear precursor into the chromane spiroketal core of the metalloproteinase-3 inhibitor berkelic acid by an acid-catalyzed deprotection/Michael addition/acetalization cascade. This efficient route resulted from the realization that the originally proposed structure is neither thermodynamically nor kinetically favored and has led to revision of the structure.