ArticleAngewandte Chemie (International ed. in English)2022
Total Synthesis of (+)-Cochlearol B by an Approach Based on a Catellani Reaction and Visible-Light-Enabled [2+2] Cycloaddition.
Article in Angewandte Chemie (International ed. in English), 2022. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 15 papers.
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15 citing papers in PubMed.
- Total syntheses of (+)-dalesconols A and B enabled by triple-relayed remote chirality transfer.Nature communications · 2026Article
- Kabbe condensation: a comprehensive review of spirochromanone synthesis and medicinal applications.RSC advances · 2026Review
- Visible-Light Mediated Activation of 1,3-Dienes and Allenes via Energy Transfers.Chemistry (Weinheim an der Bergstrasse, Germany) · 2025Review
- Harnessing Photochemistry in Natural Product Synthesis: From Strategy to Applications.Journal of natural products · 2025Review
- Total Synthesis of (-)-Psathyrin A Enabled by Radical Cyclization.Journal of the American Chemical Society · 2025Article
- Concise Total Syntheses of Leuconoxine-Type Alkaloids Enabled by Palladium/Norbornene-Catalyzed Pyrrole Difunctionalization.Angewandte Chemie (International ed. in English) · 2025Article
- Asymmetric total synthesis of benzenoid cephalotane-type diterpenoids through a cascade C(spNature communications · 2025Article
- Evolution of a Strategy for the Total Synthesis of theChemistryEurope · 2025Article
- Chemical Synthesis and Antifibrotic Properties of (±)-Cochlearol T, (±)-Ganocochlearin A, and (±)-Cochlearol Y.ACS medicinal chemistry letters · 2024Article
- Total Synthesis of Ganoapplanin Enabled by a Radical Addition/Aldol Reaction Cascade.Journal of the American Chemical Society · 2024Article
- Recent advances in the application of [2 + 2] cycloaddition in the chemical synthesis of cyclobutane-containing natural products.Natural products and bioprospecting · 2024Review
- Enantioselective total synthesis of (‒)-lucidumone enabled by tandem prins cyclization/cycloetherification sequence.Nature communications · 2024Article
- Article
- Manipulations of phenylnorbornyl palladium species for multicomponent construction of a bridged polycyclic privileged scaffold.Communications chemistry · 2022Article
- Total Synthesis of (+)-Cochlearol B by an Approach Based on a Catellani Reaction and Visible-Light-Enabled [2+2] Cycloaddition.Angewandte Chemie (International ed. in English) · 2022Article
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5 authors.
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No grant is acknowledged in the PubMed record.
Abstract
A 14-step synthesis of (+)-cochlearol B is reported. This renoprotective meroterpenoid features a unique core structure containing a densely substituted cyclobutane ring with three stereocenters. Our strategy employed an organocatalytic Kabbe condensation in route to the key chromenyl triflate. A subsequent Catellani reaction incorporated the remaining carbon atoms featured in the skeleton of cochlearol B. An ensuing visible-light-mediated [2+2] photocycloaddition closed the cyclobutane and formed the central bicyclo[3.2.0]heptane core. Notably, careful design and tuning of the Catellani and photocycloaddition reactions proved crucial in overcoming undesired reactivity, including cyclopropanation reactions and [4+2] cycloadditions.
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