ArticleJournal of the American Chemical Society2019
Synthesis of (±)-Idarubicinone via Global Functionalization of Tetracene.
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 8 papers.
What it found
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The abstract states no effect estimate the extractor could read, or names no intervention and outcome on the map, so this paper lights no cell and moves no belief. It is still indexed, cited and linked below.
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Who cites it
8 citing papers in PubMed, 22 citations in OpenAlex.
- Reimagining Dearomatization: Arenophile-Mediated Single-Atom Insertions and π-Extensions.Accounts of chemical research · 2025Article
- Copper-Catalyzed Dearomative 1,2-Hydroamination.Angewandte Chemie (International ed. in English) · 2024Article
- Dearomative logic in natural product total synthesis.Natural product reports · 2022Review
- Current Status and Trends of Research on Anthracycline-Induced Cardiotoxicity from 2002 to 2021: A Twenty-Year Bibliometric and Visualization Analysis.Oxidative medicine and cellular longevity · 2022Article
- Electrophilic Aminating Agents in Total Synthesis.Angewandte Chemie (International ed. in English) · 2021Review
- Recent Visible Light and Metal Free Strategies in [2+2] and [4+2] Photocycloadditions.European journal of organic chemistry · 2021Review
- Development of a Scalable and Sublimation-Free Route to MTAD.Organic process research & development · 2020Article
- Visible-Light-Induced Dearomatizations.European journal of organic chemistry · 2020Article
Corrections and comments
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Authors and funding
3 authors at 1 institution in 1 country.
Funding
Abstract
Anthracyclines are archetypal representatives of the tetracyclic type II polyketide natural products that are widely used in cancer chemotherapy. Although the synthesis of this class of compounds has been a subject of several investigations, all known approaches are based on annulations, relying on the union of properly prefunctionalized building blocks. Herein, we describe a conceptually different approach using a polynuclear arene as a starting template, ideally requiring only functional decorations to reach the desired target molecule. Specifically, tetracene was converted to (±)-idarubicinone, the aglycone of the FDA approved anthracycline idarubicin, through the judicious orchestration of Co- and Ru-catalyzed arene oxidation and arenophile-mediated dearomative hydroboration. Such a global functionalization strategy, the combination of site-selective arene and dearomative functionalization, provided the key anthracycline framework in five operations and enabled rapid and controlled access to (±)-idarubicinone.
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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.