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    A Concise, Phosphate-Mediated Approach to the Total Synthesis of (−)-Tetrahydrolipstatin

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    Issue Date
    2010-04
    Author
    Venukadasula, Phanindra K. M.
    Chegondi, Rambabu
    Maitra, Soma
    Hanson, Paul R.
    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/ol1002913
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    Abstract
    An efficient synthesis of (−)-tetrahydrolipstatin (THL) is reported. This method takes advantage of a phosphate tether-mediated, one-pot, sequential RCM/CM/hydrogenation protocol to deliver THL in 8 total steps from a readily prepared (S,S)-triene. The strategy incorporates selective cross metathesis, regio-selective hydrogenation, regio- and diastereoselective cuprate addition and Mitsunobu inversion for installation of the C5 formamide ester subunit.
    URI
    http://hdl.handle.net/1808/23359
    DOI
    https://doi.org/10.1021/ol1002913
    Collections
    • Chemistry Scholarly Works [616]
    Citation
    Venukadasula, P. K. M., Chegondi, R., Maitra, S., & Hanson, P. R. (2010). A Concise, Phosphate-Mediated Approach to the Total Synthesis of (−)-Tetrahydrolipstatin. Organic Letters, 12(7), 1556–1559. http://doi.org/10.1021/ol1002913

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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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