ArticleChemical science2024
Divergent total syntheses of pyrroloiminoquinone alkaloids enabled by the development of a Larock/Buchwald-Hartwig annulation/cyclization.
Article in Chemical science, 2024. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 6 papers.
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6 citing papers in PubMed.
- Evolution of Strategies Toward the Total Synthesis of Aleutianamine.The Journal of organic chemistry · 2026Article
- Optimized Biomimetic Syntheses of Discorhabdin B and Aleutianamine Drives a Deeper Exploration of Their Anticancer Potential.Journal of the American Chemical Society · 2026Article
- Marine natural products.Natural product reports · 2026Review
- Aleutianamine B, A Novel Chiral Sulfoxide Isolated fromJournal of natural products · 2026Article
- Synthesis of the Pentacyclic Core of Sanguinone B Enabled by Alkyne Functionalization.Organic letters · 2025Article
- A Divergent Synthesis of Numerous Pyrroloiminoquinone Alkaloids Identifies Promising Antiprotozoal Agents.Journal of the American Chemical Society · 2024Article
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Authors and funding
6 authors.
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Abstract
Pyrroloiminoquinone alkaloids are a large class of natural products that display a wide range of biological activities. Synthetic approaches to these natural products typically rely on a common late-stage C10-oxygenated pyrroloiminoquinone intermediate, but these strategies often lead to lengthy synthetic sequences that are not amenable to divergent syntheses. We devised an alternative approach aimed at the early introduction of the C10 nitrogen, which we hypothesized would enable late-stage diversification. This strategy hinged upon a Larock/Buchwald-Hartwig annulation/cyclization to quickly access the core of these alkaloids. We report the development of this cascade process, which was facilitated by a dual ligand system in addition to selective functionalization of the key intermediate, to provide efficient syntheses of makaluvamines A, C, and D and isobatzelline B, and the first total synthesis of makaluvamine N.
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