ArticleJournal of the American Chemical Society2017
Synthesis of ent-[3]-Ladderanol: Development and Application of Intramolecular Chirality Transfer [2+2] Cycloadditions of Allenic Ketones and Alkenes.
Article in Journal of the American Chemical Society, 2017. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 17 papers.
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Who cites it
17 citing papers in PubMed.
- Concise synthesis and strain-release diversification of bridgehead-substituted [2]-ladderanes.Nature chemistry · 2026Article
- Enantioselective Synthesis of α-Arylated Allene Ketones Through Sequential Bismuth(V)-mediated Arylation and Organocatalytic Protonation.Angewandte Chemie (International ed. in English) · 2025Article
- Recent advances in the application of [2 + 2] cycloaddition in the chemical synthesis of cyclobutane-containing natural products.Natural products and bioprospecting · 2024Review
- Tandem Isomerization/α,β-Site-Selective and Enantioselective Addition Reactions ofJournal of the American Chemical Society · 2023Article
- Lewis Acid-Promoted [2 + 2] Cycloadditions of Allenes and Ketenes: Versatile Methods for Natural Product Synthesis.Accounts of chemical research · 2023Article
- Unveiling the Chemistry and Synthetic Potential of Catalytic Cycloaddition Reaction of Allenes: A Review.Molecules (Basel, Switzerland) · 2023Review
- [2]-Ladderanes as isosteres for meta-substituted aromatic rings and rigidified cyclohexanes.Nature communications · 2022Article
- Stereoselective [2+2]-Cycloadditions of chiral allenic ketones and alkenes: Applications towards the synthesis of benzocyclobutenes and endiandric acids.Tetrahedron · 2022Article
- Preparation and Synthetic Applications of Five-to-Seven-Membered Cyclic α-Diazo Monocarbonyl Compounds.Molecules (Basel, Switzerland) · 2022Review
- Total Synthesis and Anti-Inflammatory Bioactivity of (-)-Majusculoic Acid and Its Derivatives.Marine drugs · 2021Article
- Ladderane Natural Products: From the Ground Up.Chemistry (Weinheim an der Bergstrasse, Germany) · 2021Review
- Enantioselective Synthesis of (+)-Hippolide J and Reevaluation of Antifungal Activity.Organic letters · 2020Article
- Evolution of a Strategy for the Enantioselective Synthesis of (-)-Cajanusine.Journal of the American Chemical Society · 2020Article
- Lessons in Strain and Stability: Enantioselective Synthesis of (+)-[5]-Ladderanoic Acid.Angewandte Chemie (International ed. in English) · 2020Article
- Copper Hydride Catalyzed Enantioselective Synthesis of Axially Chiral 1,3-Disubstituted Allenes.Journal of the American Chemical Society · 2019Article
- Thioallenoates in Catalytic Enantioselective [2+2]-Cycloadditions with Unactivated Alkenes.Tetrahedron · 2019Article
- H-bonded reusable template assisted para-selective ketonisation using soft electrophilic vinyl ethers.Nature communications · 2018Article
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4 authors.
Funding
Abstract
An enantioselective synthesis of ent-[3]-ladderanol is presented. The ladderanes are an interesting class of molecules for their unique structure of fused cyclobutane rings as well as their perceived biological function of organism protection. The route hinges on the development and application of a chirality transfer [2+2] cycloaddition of an allenic ketone and alkene. Further stereocontrolled transformations allowed for completion of the synthesis. The scope of the chirality transfer [2+2] cycloaddition is also presented.
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Registered trials
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