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Total Synthesis of (±)-Hirsutine: Application of Phosphine-Catalyzed Imine–Allene [4 + 2] Annulation
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    Total Synthesis of (±)-Hirsutine: Application of Phosphine-Catalyzed Imine–Allene [4 + 2] Annulation
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    Department of Chemistry and Biochemistry, University of California, Los Angeles, California 90095-1569, United States
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    Organic Letters

    Cite this: Org. Lett. 2012, 14, 17, 4634–4637
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    https://doi.org/10.1021/ol302077n
    Published August 24, 2012
    Copyright © 2012 American Chemical Society

    Abstract

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    The total synthesis of the indole alkaloid hirsutine has been achieved, with a key step being the application of our phosphine-catalyzed [4 + 2] annulation of an imine with ethyl α-methylallenoate. From commercially available indole-2-carboxaldehyde, the target was synthesized in 14 steps and 6.7% overall yield.

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    Representative experimental procedures and spectral data for all new compounds. Crystallographic data for compounds 18 and 19. This material is available free of charge via the Internet at http://pubs.acs.org.

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    Organic Letters

    Cite this: Org. Lett. 2012, 14, 17, 4634–4637
    Click to copy citationCitation copied!
    https://doi.org/10.1021/ol302077n
    Published August 24, 2012
    Copyright © 2012 American Chemical Society

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