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  A Synthesis-Driven Structure Revision of Berkelic Acid Methyl Ester

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.

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Item Permalink: https://hdl.handle.net/11858/00-001M-0000-0024-B3C7-3 Version Permalink: https://hdl.handle.net/11858/00-001M-0000-0024-B3C8-1
Genre: Journal Article

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 Creators:
Buchgraber, Philipp1, Author           
Snaddon, Thomas N.1, Author           
Wirtz, Cornelia2, Author           
Mynott, Richard2, Author           
Goddard, Richard3, Author           
Fürstner, Alois1, Author           
Affiliations:
1Research Department Fürstner, Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_1445584              
2Service Department Mynott (NMR), Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_1445627              
3Service Department Lehmann (EMR), Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_1445625              

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Free keywords: anticancer agents; enzyme inhibitors; natural products; spiroacetals; structure elucidation
 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.

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Language(s): eng - English
 Dates: 2008-07-092008-09-242008-10-20
 Publication Status: Issued
 Pages: 5
 Publishing info: -
 Table of Contents: -
 Rev. Type: Peer
 Identifiers: DOI: 10.1002/anie.200803339
 Degree: -

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Title: Angewandte Chemie International Edition
  Abbreviation : Angew. Chem. Int. Ed.
Source Genre: Journal
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Publ. Info: Weinheim : Wiley-VCH Verlag
Pages: - Volume / Issue: 47 (44) Sequence Number: - Start / End Page: 8450 - 8454 Identifier: ISSN: 1521-3773
CoNE: https://pure.mpg.de/cone/journals/resource/0570-0833