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    Synthesis of Cruentaren A

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    Issue Date
    2012-12-21
    Author
    Kusuma, Bhaskar Reddy
    Brandt, Gary E. L.
    Blagg, Brian S. J.
    Publisher
    American Chemical Society
    Type
    Article
    Article Version
    Scholarly/refereed, author accepted manuscript
    Rights
    This document is the Accepted Manuscript version of a Published Work that appeared in final form in Organic Letters, copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see http://dx.doi.org/10.1021/ol302999v.
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    Abstract
    Cruentaren A, an antifungal benzolactone produced by the myxobacterium Byssovorax cruenta, is highly cytotoxic against various human cancer cell lines and a highly selective inhibitor of mitochondrial F-ATPase. A convergent and efficient synthesis of cruentaren A is reported, based upon a diastereoselective alkylation, a series of stereoselective aldol reactions utilizing Myers’ pseudoephedrine propionamide, an acyl bromide–mediated esterification and a ring-closing metathesis (RCM) as the key steps. The RCM reaction was applied for the first time towards the total synthesis of cruentaren A, which led to a convergent and efficient synthesis of the natural product.
    URI
    http://hdl.handle.net/1808/23500
    DOI
    https://doi.org/10.1021/ol302999v
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    • Chemistry Scholarly Works [610]
    Citation
    Kusuma, B. R., Brandt, G. E. L., & Blagg, B. S. J. (2012). Synthesis of Cruentaren A. Organic Letters, 14(24), 6242–6245. http://doi.org/10.1021/ol302999v

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    Contact KU ScholarWorks
    785-864-8983
    KU Libraries
    1425 Jayhawk Blvd
    Lawrence, KS 66045
    785-864-8983

    KU Libraries
    1425 Jayhawk Blvd
    Lawrence, KS 66045
    Image Credits
     

     

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