ArticleThe Journal of organic chemistry2014
C7-derivatization of C3-alkylindoles including tryptophans and tryptamines.
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 27 papers.
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Who cites it
27 citing papers in PubMed.
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- Total synthesis of asperdinones B, C, D, E and terezine D.Beilstein journal of organic chemistry · 2025Article
- Unified, Biosynthesis-Inspired, Completely Stereocontrolled Total Synthesis of All Highest-Order [n + 1] Oligocyclotryptamine Alkaloids.Journal of the American Chemical Society · 2024Article
- Preparation ofInternational journal of molecular sciences · 2023Article
- Divergent total syntheses of ITHQ-type bis-β-carboline alkaloids by regio-selective formal aza-[4 + 2] cycloaddition and late-stage C-H functionalization.Chemical science · 2023Article
- Total synthesis of complex 2,5-diketopiperazine alkaloids.The Alkaloids. Chemistry and biology · 2023Review
- Indolactam Dipeptides as Nanomolar Gli Inhibitors.ACS medicinal chemistry letters · 2022Article
- Selective Labeling of Peptides with o-Carboranes via Manganese(I)-Catalyzed C-H Activation.Chemistry (Weinheim an der Bergstrasse, Germany) · 2022Article
- Total Synthesis of (-)-Kopsifoline A and (+)-Kopsifoline E.Organic letters · 2021Article
- Double Arylation of the Indole Side Chain of Tri- and Tetrapodal Tryptophan Derivatives Renders Highly Potent HIV-1 and EV-A71 Entry Inhibitors†.Journal of medicinal chemistry · 2021Article
- Staurosporine Analogs Via C-H Borylation.ACS medicinal chemistry letters · 2020Article
- Boron Accumulation in Brain Tumor Cells through Boc-Protected Tryptophan as a Carrier for Boron Neutron Capture Therapy.ACS medicinal chemistry letters · 2020Article
- Acyl-Directed ortho-Borylation of Anilines and C7 Borylation of Indoles using just BBrAngewandte Chemie (International ed. in English) · 2019Article
- Indolylboronic Acids: Preparation and Applications.Molecules (Basel, Switzerland) · 2019Review
- A Convenient C-H Functionalization Platform for Pyrroloiminoquinone Alkaloid Synthesis.Tetrahedron · 2019Article
- 1,2-Azaborine's Distinct Electronic Structure Unlocks Two New Regioisomeric Building Blocks via Resolution Chemistry.Journal of the American Chemical Society · 2019Article
- Development of Mithramycin Analogues with Increased Selectivity toward ETS Transcription Factor Expressing Cancers.Journal of medicinal chemistry · 2018Article
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Authors and funding
6 authors.
Funding
Abstract
A versatile strategy for C7-selective boronation of tryptophans, tryptamines, and 3-alkylindoles by way of a single-pot C2/C7-diboronation-C2-protodeboronation sequence is described. The combination of a mild iridium-catalyzed C2/C7-diboronation followed by an in situ palladium-catalyzed C2-protodeboronation allows efficient entry to valuable C7-boroindoles that enable further C7-derivatization. The versatility of the chemistry is highlighted by the gram-scale synthesis of C7-boronated N-Boc-L-tryptophan methyl ester and the rapid synthesis of C7-halo, C7-hydroxy, and C7-aryl tryptophan derivatives.
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