ArticleAngewandte Chemie (International ed. in English)2022
Enantioselective Total Synthesis of (-)-Limaspermidine and (-)-Kopsinine by a Nitroaryl Transfer Cascade Strategy.
Article in Angewandte Chemie (International ed. in English), 2022. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 9 papers.
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9 citing papers in PubMed.
- Recent Advances in the Synthesis of Spiroindolines: Catalytic Strategies, Stereoselectivity, and Synthetic Utility (2020-2025).Molecules (Basel, Switzerland) · 2026Review
- Smiles-Truce Cascades Enable Heteroaryl Cyclopropane and Sultine Synthesis.Angewandte Chemie (International ed. in English) · 2025Article
- Total Synthesis of (+)-Paucidactine D.The Journal of organic chemistry · 2025Article
- Aza-Achmatowicz rearrangement coupled with intermolecular aza-Friedel-Crafts enables total syntheses of uleine and aspidosperma alkaloids.Chemical science · 2024Article
- Enantioselective Total Synthesis of (-)-Hunterine A Enabled by a Desymmetrization/Rearrangement Strategy.Journal of the American Chemical Society · 2024Article
- Aryne-Enabled C-N Arylation of Anilines.Angewandte Chemie (International ed. in English) · 2023Article
- Synthesis of Functionalized Pyrrolidinone Scaffolds via Smiles-Truce Cascade.Organic letters · 2023Article
- An NHC-Catalyzed Desulfonylative Smiles Rearrangement of Pyrrole and Indole Carboxaldehydes.The Journal of organic chemistry · 2023Article
- Enantioselective Total Synthesis of (-)-Limaspermidine and (-)-Kopsinine by a Nitroaryl Transfer Cascade Strategy.Angewandte Chemie (International ed. in English) · 2022Article
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5 authors.
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Abstract
We report an intramolecular conjugate addition/Truce-Smiles/E1cb cascade of 2-nitrobenzenesulfonamide-functionalized cyclohexenones as a new entry to the core scaffold of monoterpene indole alkaloids. The method was applied to the asymmetric total synthesis of (-)-limaspermidine, (-)-kopsinilam, and (-)-kopsinine, as well as the framework of the kopsifoline alkaloids, thus highlighting its complementarity to existing approaches involving the use of indole-based starting materials or the interrupted Fischer indole synthesis. Furthermore, we show that the cascade tolerates various substituents on the nitroarene, opening the way to other natural products as well as non-natural analogues.
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