Recently the pyrroloindoline natural products peganine A and B were isolated from the seeds of Peganum harmala. These pyrroloindolines have an unusual carbon skeleton with a methyl group at C2 of the pyrroloindoline core. To access these natural products a new method for the synthesis of pyrroloindolines that are oxygenated at the C3a was developed utilizing an oxidative cyclization of tryptamines employing the oxoammonium salt 4-acetamido-2,2,6,6-tetramethyl-1-oxopiperidinium tetrafluoroborate. This oxidizing agent effectively cyclizes tryptamine derivatives to access the core structure of the peganine natural products as well as a number of other pyrroloindolines. The substrate scope of the oxidative cyclization and its application to the synthesis of the peganines will be described.<br/>

Synthetic studies on peganine A and B

Macromolecular Chemistry: The Second Century

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ACS Spring 2020 National Meeting & Expo

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.