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    Total Syntheses of Arylindolizidine Alkaloids (+)-Ipalbidine and (+)-Antofine

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    Issue Date
    2010-09-03
    Author
    Niphakis, Micah James
    Georg, Gunda I.
    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/jo101051w.
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    Abstract
    This paper presents the first application of two recently developed reactions to natural product synthesis. The first method involves a 6-endo-trig cyclization to prepare a versatile chiral enaminone building block. The second is a direct C–H arylation reaction. As a showcase for the utility of these methods, (+)-antofine and (+)-ipalbidine were synthesized in only 8 steps and 24–26% overall yields.
    URI
    http://hdl.handle.net/1808/23697
    DOI
    https://doi.org/10.1021/jo101051w
    Collections
    • Medicinal Chemistry Scholarly Works [196]
    Citation
    Niphakis, M. J., & Georg, G. I. (2010). Total Syntheses of Arylindolizidine Alkaloids (+)-Ipalbidine and (+)-Antofine. The Journal of Organic Chemistry, 75(17), 6019–6022. http://doi.org/10.1021/jo101051w

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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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