ArticleOrganic letters2021
Total Synthesis of (-)-Kopsifoline A and (+)-Kopsifoline E.
Article in Organic letters, 2021. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 10 papers.
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Who cites it
10 citing papers in PubMed.
- Total Synthesis of the Spirocyclic Bis-Indole Alkaloid (-)-Owerreine via a [4+2] Annulation.Angewandte Chemie (International ed. in English) · 2026Article
- Electronic Activation Enables the Borylation of Alkyl C-H Bonds in Saturated Nitrogen Heterocycles.Journal of the American Chemical Society · 2025Article
- Total Synthesis of (-)-Owerreine and (-)-Anhydrovobtusine.Organic letters · 2025Article
- The Importance of Atomic Charges for Predicting Site-Selective Ir-, Ru-, and Rh-Catalyzed C-H Borylations.The Journal of organic chemistry · 2025Article
- Review
- Aza-Achmatowicz rearrangement coupled with intermolecular aza-Friedel-Crafts enables total syntheses of uleine and aspidosperma alkaloids.Chemical science · 2024Article
- Enantioselective Total Synthesis of (-)-Limaspermidine and (-)-Kopsinine by a Nitroaryl Transfer Cascade Strategy.Angewandte Chemie (International ed. in English) · 2022Article
- Total Synthesis of (-)-Voacinol and (-)-Voacandimine C.Journal of the American Chemical Society · 2022Article
- Semi-syntheses and interrogation of indole-substitutedOrganic & biomolecular chemistry · 2022Article
- Total Synthesis of (-)-Kopsifoline A and (+)-Kopsifoline E.Organic letters · 2021Article
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Authors and funding
3 authors.
Funding
Abstract
We report the first total synthesis of (-)-kopsifoline A and (+)-kopsifoline E. Our synthetic strategy features a biogenetically inspired regioselective C17-functionalization of a versatile intermediate containing the pentacyclic core of aspidosperma alkaloids. The vinylogous urethane substructure of this intermediate affords (-)-kopsifoline D via C3-C21 bond formation under the Mitsunobu reaction conditions, while it enables selective C17-functionalization en route to (-)-kopsifoline A and (+)-kopsifoline E.
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