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Discovery and Total Synthesis of a Bis(cyclotryptamine) Alkaloid Bearing the Elusive Piperidinoindoline Scaffold

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    Discovery and Total Synthesis of a Bis(cyclotryptamine) Alkaloid Bearing the Elusive Piperidinoindoline Scaffold
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    Journal of the American Chemical Society

    Cite this: J. Am. Chem. Soc. 2020, 142, 27, 11685–11690
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    https://doi.org/10.1021/jacs.0c04760
    Published June 10, 2020
    Copyright © 2020 American Chemical Society
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    Abstract

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    Bis(cyclotryptamine) alkaloids have been popular topics of study for many decades. Five possible scaffolds for bis(cyclotryptamine) alkaloids were originally postulated in the 1950s, but only four of these scaffolds have been observed in natural products to date. We describe synthetic access to the elusive fifth scaffold, the piperidinoindoline, through syntheses of compounds now termed “dihydropsychotriadine” and “psychotriadine”. The latter of these compounds was subsequently identified in extracts of the flower Psychotria colorata. Our synthetic route features a stereospecific solid-state photodecarbonylation reaction to introduce the key vicinal quaternary stereocenters.

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    Journal of the American Chemical Society

    Cite this: J. Am. Chem. Soc. 2020, 142, 27, 11685–11690
    Click to copy citationCitation copied!
    https://doi.org/10.1021/jacs.0c04760
    Published June 10, 2020
    Copyright © 2020 American Chemical Society
    Request reuse permissions

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