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

ABSTRACT: 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.

SUBMITTER: Dotson JJ

PROVIDER: S-EPMC8299283 | biostudies-literature | 2020 Jul

REPOSITORIES: biostudies-literature

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

Dotson Jordan J JJ Bachman J Logan JL Garcia-Garibay Miguel A MA Garg Neil K NK

Journal of the American Chemical Society 20200623 27

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 ext ...[more]

PMID: 32520547

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