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Synthesis of the Azaphilones (+)-Sclerotiorin and (+)-8-O-Methylsclerotiorinamine Utilizing (+)-Sparteine Surrogates in Copper-Mediated Oxidative Dearomatization

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    Synthesis of the Azaphilones (+)-Sclerotiorin and (+)-8-O-Methylsclerotiorinamine Utilizing (+)-Sparteine Surrogates in Copper-Mediated Oxidative Dearomatization
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    † Department of Chemistry, Center for Chemical Methodology and Library Development (CMLD-BU), Boston University, 590 Commonwealth Avenue, Boston, Massachusetts 02215, United States
    ‡ Department of Chemistry, University of York, Heslington, York YO105DD, U.K.
    *E-mail: [email protected]
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    The Journal of Organic Chemistry

    Cite this: J. Org. Chem. 2011, 76, 8, 2577–2584
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    https://doi.org/10.1021/jo102448n
    Published March 14, 2011
    Copyright © 2011 American Chemical Society
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    Abstract

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    Enantioselective syntheses of the azaphilone natural products (+)-sclerotiorin and (+)-8-O-methylsclerotiorinamine that possess the natural R-configuration at the quaternary center are reported. The syntheses were accomplished using copper-mediated asymmetric dearomatization employing bis-μ-oxo copper complexes prepared from readily available (+)-sparteine surrogates. Of note, site-selective O-methylation of a vinylogous pyridone was used to access the isoquinolin-6(7H)-one core of (+)-8-O-methylsclerotiorinamine.

    Copyright © 2011 American Chemical Society

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    The Journal of Organic Chemistry

    Cite this: J. Org. Chem. 2011, 76, 8, 2577–2584
    Click to copy citationCitation copied!
    https://doi.org/10.1021/jo102448n
    Published March 14, 2011
    Copyright © 2011 American Chemical Society
    Request reuse permissions

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