Impatien A, an isoindolone natural product isolated from <i>Corydalis impatiens,</i> and ochotensimine, a tetrahydroisoquinoline natural product isolated from<i> Corydalis ochotensis,</i> both possess a similar carbon scaffold featuring a spirocyclic stereogenic center. While ochotensimine and its des-methyl analog ochotensine have been shown to inhibit TNF-a, have been characterized as single enantiomers by optical rotation studies and by x-ray diffraction, and have been prepared via racemic syntheses, much less is known about the related impatien A. A unified approach to the preparation of the spirocyclic centers of these natural products poses a synthetic challenge both in its racemic and enantioenriched forms. We envision a metal-catalysed approach to the creation of these spirocyclic centers, which would be amenable to asymmetric induction. From readily available starting material, the southern indane half (identical to both natural products) and an appropriate northern arene half tagged with a cross-coupling handle can be synthesized with minimal chromatographic steps. Key palladium-catalysed arylation and cyclization allow for the construction of the spirocyclic framework.

Progress towards the total syntheses of Impatien A and Ochotensimine: Utilizing a novel cyclization

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.