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The Total Synthesis of (−)-Scabrolide A

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    The Total Synthesis of (−)-Scabrolide A
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    • Nicholas J. Hafeman
      Nicholas J. Hafeman
      The Warren and Katharine Schlinger Laboratory for Chemistry and Chemical Engineering, Division of Chemistry and Chemical Engineering, California Institute of Technology, MC 101-20, Pasadena, California 91125, United States
      More by Nicholas J. Hafeman
      Orcidhttp://orcid.org/0000-0001-7525-7597
    • Steven A. Loskot
      Steven A. Loskot
      The Warren and Katharine Schlinger Laboratory for Chemistry and Chemical Engineering, Division of Chemistry and Chemical Engineering, California Institute of Technology, MC 101-20, Pasadena, California 91125, United States
      More by Steven A. Loskot
    • Christopher E. Reimann
      Christopher E. Reimann
      The Warren and Katharine Schlinger Laboratory for Chemistry and Chemical Engineering, Division of Chemistry and Chemical Engineering, California Institute of Technology, MC 101-20, Pasadena, California 91125, United States
      More by Christopher E. Reimann
    • Beau P. Pritchett
      Beau P. Pritchett
      The Warren and Katharine Schlinger Laboratory for Chemistry and Chemical Engineering, Division of Chemistry and Chemical Engineering, California Institute of Technology, MC 101-20, Pasadena, California 91125, United States
      More by Beau P. Pritchett
    • Scott C. Virgil
      Scott C. Virgil
      The Warren and Katharine Schlinger Laboratory for Chemistry and Chemical Engineering, Division of Chemistry and Chemical Engineering, California Institute of Technology, MC 101-20, Pasadena, California 91125, United States
      More by Scott C. Virgil
    • Brian M. Stoltz*
      Brian M. Stoltz
      The Warren and Katharine Schlinger Laboratory for Chemistry and Chemical Engineering, Division of Chemistry and Chemical Engineering, California Institute of Technology, MC 101-20, Pasadena, California 91125, United States
      *[email protected]
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      Orcidhttp://orcid.org/0000-0001-9837-1528
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    Journal of the American Chemical Society

    Cite this: J. Am. Chem. Soc. 2020, 142, 19, 8585–8590
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    https://doi.org/10.1021/jacs.0c02513
    Published March 30, 2020
    Copyright © 2020 American Chemical Society
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    Abstract

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    The first total synthesis of the norcembranoid diterpenoid scabrolide A is disclosed. The route begins with the synthesis of two chiral pool-derived fragments, which undergo a convergent coupling to expediently introduce all 19 carbon atoms of the natural product. An intramolecular Diels–Alder reaction and an enone–olefin cycloaddition/fragmentation sequence are then employed to construct the fused [5–6–7] linear carbocyclic core of the molecule and complete the total synthesis.

    Copyright © 2020 American Chemical Society

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    This article is cited by 43 publications.

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    Journal of the American Chemical Society

    Cite this: J. Am. Chem. Soc. 2020, 142, 19, 8585–8590
    Click to copy citationCitation copied!
    https://doi.org/10.1021/jacs.0c02513
    Published March 30, 2020
    Copyright © 2020 American Chemical Society
    Request reuse permissions

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