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    Total Synthesis of Dolabelide C: A Phosphate-Mediated Approach

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    Issue Date
    2011-06-03
    Author
    Hanson, Paul R.
    Chegondi, Rambabu
    Nguyen, John
    Thomas, Christopher Daniel
    Waetzig, Joshua David
    Whitehead, Alan
    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 the Journal of Organic Chemistry, 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/jo2003506.
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    Abstract
    The first synthesis of dolabelide C (1), a cytotoxic marine macrolide, is reported utilizing a phosphate tether-mediated approach. Bicyclic phosphates (S,S,SP)-5 and (R,R,RP)-5 serve as the central building blocks for the construction of two major 1,3-anti-diol subunits in 1 through selective cleavage pathways, regioselective olefin reduction and cross-metathesis. Overall, phosphate-mediated processes provided copious amounts of both major subunits allowing for a detailed RCM macrocyclization study to the 24-membered macrolactone 1.
    URI
    http://hdl.handle.net/1808/23726
    DOI
    https://doi.org/10.1021/jo2003506
    Collections
    • Chemistry Scholarly Works [601]
    Citation
    Hanson, P. R., Chegondi, R., Nguyen, J., Thomas, C. D., Waetzig, J. D., & Whitehead, A. (2011). Total Synthesis of Dolabelide C: A Phosphate-Mediated Approach. The Journal of Organic Chemistry, 76(11), 4358–4370. http://doi.org/10.1021/jo2003506

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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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