ArticleThe Journal of organic chemistry2014
Total synthesis, stereochemical assignment, and biological activity of all known (-)-trigonoliimines.
Article in The Journal of organic chemistry, 2014. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 14 papers.
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Who cites it
14 citing papers in PubMed.
- Highly Active CH Bond Borylation of Aromatics With Pyridine as Convenient, Low-Cost Ligand Under Iridium Catalysis.ChemSusChem · 2026Article
- Total Synthesis of (±)-Baphicacanthcusine A Enabled by Sequential Ring Contractions.Angewandte Chemie (International ed. in English) · 2024Article
- C-H functionalization of 2-alkyl tryptamines: direct assembly of azepino[4,5-Chemical science · 2024Article
- Rapid Access to 2,2-Disubstituted Indolines via Dearomative Indolic-Claisen Rearrangement: Concise, Enantioselective Total Synthesis of (+)-Hinckdentine A.Journal of the American Chemical Society · 2023Article
- Unified total synthesis of the brevianamide alkaloids enabled by chemical investigations into their biosynthesis.Chemical science · 2022Article
- Total Synthesis of (-)-Kopsifoline A and (+)-Kopsifoline E.Organic letters · 2021Article
- A general approach to 2,2-disubstituted indoxyls: total synthesis of brevianamide A and trigonoliimine C.Chemical science · 2021Article
- Electrophilically Activated Nitroalkanes in Synthesis of 3,4-Dihydroquinozalines.Molecules (Basel, Switzerland) · 2021Article
- One-Pot Tandem Assembly of Amides, Amines, and Ketones: Synthesis of C4-Quaternary 3,4- and 1,4-Dihydroquinazolines.The Journal of organic chemistry · 2020Article
- Organocatalytic Enantioselective Mannich Reaction: Direct Access to Chiral β-Amino Esters.ACS omega · 2019Article
- Electrophilic Oxidation and [1,2]-Rearrangement of the Biindole Core of Birinapant.ACS medicinal chemistry letters · 2016Article
- Asymmetric synthesis of 1H-pyrrol-3(2H)-ones from 2,3-diketoesters by combination of aldol condensation with benzilic acid rearrangement.Chemical communications (Cambridge, England) · 2016Article
- C7-derivatization of C3-alkylindoles including tryptophans and tryptamines.The Journal of organic chemistry · 2014Article
- Advances in the chemistry of oxaziridines.Chemical reviews · 2014Article
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4 authors.
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Abstract
A full account of our concise and enantioselective total syntheses of all known (-)-trigonoliimine alkaloids is described. Our retrobiosynthetic analysis of these natural products enabled identification of a single bistryptamine precursor as a precursor to all known trigonoliimines through a sequence of transformations involving asymmetric oxidation and reorganization. Our enantioselective syntheses of these alkaloids enabled the revision of the absolute stereochemistry of (-)-trigonoliimines A, B, and C. We report that trigonoliimines A, B, C and structurally related compounds showed weak anticancer activities against HeLa and U-937 cells.
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