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A 7-Step Formal Asymmetric Total Synthesis of Strictamine via an Asymmetric Propargylation and Metal-Mediated Cyclization

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    A 7-Step Formal Asymmetric Total Synthesis of Strictamine via an Asymmetric Propargylation and Metal-Mediated Cyclization
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    † Columbia University, Dept. of Chemistry, 3000 Broadway, New York, New York 10027, United States
    ‡ The Scripps Research Institute, Dept. of Chemistry, 130 Scripps Way, Jupiter, Florida 33458, United States
    § University of Chicago, Dept. of Chemistry, 5735 S. Ellis Avenue, Chicago, Illinois 60637, United States
    *E-mail: [email protected]
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    Organic Letters

    Cite this: Org. Lett. 2017, 19, 5, 1004–1007
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    https://doi.org/10.1021/acs.orglett.6b03839
    Published February 13, 2017
    Copyright © 2017 American Chemical Society
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    Abstract

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    Herein is shown how a novel catalytic asymmetric propargylation of 3,4-dihydro-β-carboline, followed by a designed Au(I)/Ag(I)-mediated 6-endo-dig cyclization, can directly deliver the indolenine-fused methanoquinolizidine core of the akuammiline alkaloid strictamine in its native oxidation state, ultimately achieving a 7-step formal asymmetric total synthesis. Also demonstrated are how the cyclization products can rearrange into vincorine-type skeletons and a further use for the developed propargylation with the first catalytic asymmetric total synthesis of decarbomethoxydihydrogambirtannine.

    Copyright © 2017 American Chemical Society

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    Organic Letters

    Cite this: Org. Lett. 2017, 19, 5, 1004–1007
    Click to copy citationCitation copied!
    https://doi.org/10.1021/acs.orglett.6b03839
    Published February 13, 2017
    Copyright © 2017 American Chemical Society
    Request reuse permissions

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