ArticleJournal of the American Chemical Society2019
Enantioselective Synthesis of Isocarbostyril Alkaloids and Analogs Using Catalytic Dearomative Functionalization of Benzene.
Article in Journal of the American Chemical Society, 2019. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 23 papers.
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Who cites it
23 citing papers in PubMed.
- Single-cell sequencing-guided discovery of narciclasine as a dual VCAM-1/ICAM-1 inhibitor for atherosclerosis management.Genes & diseases · 2027Article
- Overcoming Docetaxel Resistance in Prostate Cancer by Targeting Cell Cycle Progression with Narciclasine-Based Compounds.ACS omega · 2026Article
- Narciclasine as a Novel Treatment for Lung Cancer and Malignant Pleural Mesothelioma: Insights from 3D Tumor Spheroid Models.International journal of molecular sciences · 2025Article
- Reimagining Dearomatization: Arenophile-Mediated Single-Atom Insertions and π-Extensions.Accounts of chemical research · 2025Article
- Antiparasitic Activity of Narciclasine and Evaluation of Its Effects on Plasma Membrane and Mitochondria ofACS omega · 2025Article
- Diastereodivergent Construction of Octahydrophenanthridinone and Octahydrophenanthridine Cores.Molecules (Basel, Switzerland) · 2025Article
- Copper-Catalyzed DearomativeACS catalysis · 2024Article
- Discovery and bioinspired total syntheses of unprecedented sesquiterpenoid dimers unveiled bifurcating [4 + 2] cycloaddition and target differentiation of enantiomers.Chemical science · 2024Article
- Rejuvenation of dearomative cycloaddition reactionsChemical science · 2023Review
- Site selective gold(i)-catalysed benzylic C-H aminationChemical science · 2023Article
- Dearomative logic in natural product total synthesis.Natural product reports · 2022Review
- Stereodivergent dehydrative allylation of β-keto esters using a Ru/Pd synergistic catalyst.Nature communications · 2022Article
- N-Heterocyclic carbene (NHC)-catalyzed oxidation of unactivated aldimines to amidesRSC advances · 2022Article
- Electrophilic Aminating Agents in Total Synthesis.Angewandte Chemie (International ed. in English) · 2021Review
- Short, enantioselective, gram-scale synthesis of (-)-zephyranthine.Chemical science · 2021Article
- Recent Visible Light and Metal Free Strategies in [2+2] and [4+2] Photocycloadditions.European journal of organic chemistry · 2021Review
- Theoretical Analysis of the Heterocyclic [4+2] Cycloaddition Between Pyridinium Ion and Enol Ether.ChemistryOpen · 2021Article
- Advances in Catalytic Asymmetric Dearomatization.ACS central science · 2021Review
- Development of a Scalable and Sublimation-Free Route to MTAD.Organic process research & development · 2020Article
- Total synthesis of endiandric acid J and beilcyclone A from cyclooctatetraene.Chemical science · 2020Article
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Authors and funding
6 authors.
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Abstract
Enantioselective total syntheses of the anticancer isocarbostyril alkaloids (+)-7-deoxypancratistatin, (+)-pancratistatin, (+)-lycoricidine, and (+)-narciclasine are described. Our strategy for accessing this unique class of natural products is based on the development of a Ni-catalyzed dearomative trans-1,2-carboamination of benzene. The effectiveness of this dearomatization approach is notable, as only two additional olefin functionalizations are needed to construct the fully decorated aminocyclitol cores of these alkaloids. Installation of the lactam ring has been achieved through several pathways and a direct interconversion between natural products was established via a late-stage C-7 cupration. Using this synthetic blueprint, we were able to produce natural products on a gram scale and provide tailored analogs with improved activity, solubility, and metabolic stability.
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