ArticleAngewandte Chemie (International ed. in English)2017
Total Synthesis of Lycoricidine and Narciclasine by Chemical Dearomatization of Bromobenzene.
Article in Angewandte Chemie (International ed. in English), 2017. 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, 52 citations in OpenAlex.
- 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
- Conversion of Natural Narciclasine to Its C-1 and C-6 Derivatives and Their Antitumor Activity Evaluation: Some Unusual Chemistry of Narciclasine.Molecules (Basel, Switzerland) · 2022Article
- Short, enantioselective, gram-scale synthesis of (-)-zephyranthine.Chemical science · 2021Article
- Development of a Scalable and Sublimation-Free Route to MTAD.Organic process research & development · 2020Article
- Narciclasine, an isocarbostyril alkaloid, has preferential activity against primary effusion lymphoma.Scientific reports · 2020Article
- Visible-Light-Induced Dearomatizations.European journal of organic chemistry · 2020Article
- Enantioselective Synthesis of Isocarbostyril Alkaloids and Analogs Using Catalytic Dearomative Functionalization of Benzene.Journal of the American Chemical Society · 2019Article
- Narciclasine induces autophagy-dependent apoptosis in triple-negative breast cancer cells by regulating the AMPK-ULK1 axis.Cell proliferation · 2018Article
Corrections and comments
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Authors and funding
3 authors at 1 institution in 1 country.
Funding
Abstract
The total synthesis of lycoricidine and narciclasine is enabled by an arenophile-mediated dearomative dihydroxylation of bromobenzene. Subsequent transpositive Suzuki coupling and cycloreversion deliver a key biaryl dihydrodiol intermediate, which is rapidly converted into lycoricidine through site-selective syn-1,4-hydroxyamination and deprotection. The total synthesis of narciclasine is accomplished by the late-stage, amide-directed C-H hydroxylation of a lycoricidine intermediate. Moreover, the general applicability of this strategy to access dihydroxylated biphenyls is demonstrated with several examples.
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Registered trials
Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.