ArticleNature chemical biology2013
Biomimetic diversity-oriented synthesis of benzannulated medium rings via ring expansion.
Article in Nature chemical biology, 2013. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 40 papers.
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Who cites it
40 citing papers in PubMed, 164 citations in OpenAlex.
- Modular Assembly of Macrocyclic Sulfonamides via Consecutive Cascade Ring Expansion Reactions.Chemistry (Weinheim an der Bergstrasse, Germany) · 2026Article
- An organometallic approach to the synthesis of heteropolycyclic compounds from benzenes.Nature communications · 2025Article
- Stereocontrolled four-carbon homologation of vicinally functionalized allylic pyrrolidines to highly customized azonines bearing remote benzylic stereocenters.RSC advances · 2025Article
- Medium-Sized Ring Expansion Strategies: Enhancing Small-Molecule Library Development.Molecules (Basel, Switzerland) · 2024Review
- A Lewis Acid-Promoted Michael Addition and Ring-Expansion Cascade for the Construction of Nitrogen-Containing Medium-Sized Rings.Molecules (Basel, Switzerland) · 2023Article
- Recent Advances in Divergent Synthetic Strategies for Indole-Based Natural Product Libraries.Molecules (Basel, Switzerland) · 2022Review
- Synthesis of medium-ring lactams and macrocyclic peptide mimeticsRSC chemical biology · 2022Article
- Cheminformatic analysis of natural product-based drugs and chemical probes.Natural product reports · 2022Review
- Hydantoin-bridged medium ring scaffolds by migratory insertion of urea-tethered nitrile anions into aromatic C-N bonds.Chemical science · 2020Article
- Evaluating the Viability of Successive Ring-Expansions Based on Amino Acid and Hydroxyacid Side-Chain Insertion.Chemistry (Weinheim an der Bergstrasse, Germany) · 2020Article
- A happy medium: the synthesis of medicinally important medium-sized ringsChemical science · 2020Review
- Tricyclic Imidazolidin-4-ones by Witkop Oxidation of Tetrahydro-β-carbolines.The Journal of organic chemistry · 2020Article
- A Scaffold-Diversity Synthesis of Biologically Intriguing Cyclic Sulfonamides.Chemistry (Weinheim an der Bergstrasse, Germany) · 2019Article
- A general strategy for diversifying complex natural products to polycyclic scaffolds with medium-sized rings.Nature communications · 2019Article
- Synthesis of bicyclic ethers by a palladium-catalyzed oxidative cyclization-redox relay-π-allyl-Pd cyclization cascade reaction.Chemical communications (Cambridge, England) · 2019Article
- Regio- and Diastereoselective Iron-Catalyzed [4+4]-Cycloaddition of 1,3-Dienes.Journal of the American Chemical Society · 2019Article
- A divergent synthetic pathway for pyrimidine-embedded medium-sized azacycles through an N-quaternizing strategy.Chemical science · 2019Article
- Iterative Assembly of Macrocyclic Lactones using Successive Ring Expansion Reactions.Chemistry (Weinheim an der Bergstrasse, Germany) · 2018Article
- Synthesis of Benzannulated Medium-ring Lactams via a Tandem Oxidative Dearomatization-Ring Expansion Reaction.Chemistry (Weinheim an der Bergstrasse, Germany) · 2018Article
- Chemical probes and drug leads from advances in synthetic planning and methodology.Nature reviews. Drug discovery · 2018Review
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Authors and funding
3 authors at 2 institutions in 1 country.
Funding
Abstract
Nature has exploited medium-sized 8- to 11-membered rings in a variety of natural products to address diverse and challenging biological targets. However, owing to the limitations of conventional cyclization-based approaches to medium-ring synthesis, these structures remain severely underrepresented in current probe and drug discovery efforts. To address this problem, we have established an alternative, biomimetic ring expansion approach to the diversity-oriented synthesis of medium-ring libraries. Oxidative dearomatization of bicyclic phenols affords polycyclic cyclohexadienones that undergo efficient ring expansion to form benzannulated medium-ring scaffolds found in natural products. The ring expansion reaction can be induced using three complementary reagents that avoid competing dienone-phenol rearrangements and is driven by rearomatization of a phenol ring adjacent to the scissile bond. Cheminformatic analysis of the resulting first-generation library confirms that these molecules occupy chemical space overlapping with medium-ring natural products and distinct from that of synthetic drugs and drug-like libraries.
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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.