Ergot alkaloids have been shown to exhibit useful medicinal properties such as labor inducing activity, migraine relief, mood-perception regulation. Ergotryptamine, an ergot alkaloid, was recently isolated in minute amount from Aspergillus nidulans. In order to facilitate biological studies, this compound was selected as a target for synthesis. Proposed key synthetic steps include a palladium catalyzed Kosugi-Migita-Stille cross coupling, a Mizoroki-Heck reaction, and a carbon monoxide-mediated palladium-catalyzed reductive N-heterocyclization. Using a similar synthetic approach, synthesis of two indoles norpsilocin and aurantioclavine has been envisioned in 1-2 additional steps. Norpsilocin, a component of magic mushroom with promising psychotropic effects, was recently isolated from Psilocybe cubensis. Aurantioclavine was first isolated in 1981 from the fungus Penicillium aurantiovirens. It has become an attractive target for synthesis due to its role as a biosynthetic precursor to the communesin alkaloids, which display cytotoxicity against leukemia cell lines.

Synthetic approach to ergotryptamine, norpsilocin, and aurantioclavine

2019 Fall National Meeting

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