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

Cite this: J. Am. Chem. Soc. 2020, 142, 27, 11685–11690
Publication Date (Web):June 10, 2020
https://doi.org/10.1021/jacs.0c04760
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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