ArticleNature chemistry2022
Total synthesis of nine longiborneol sesquiterpenoids using a functionalized camphor strategy.
Article in Nature chemistry, 2022. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 25 papers.
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Who cites it
25 citing papers in PubMed.
- Toward the Synthesis of Pestalustaine A: Structural Revision and Formation of Original Strained Tricyclic Architectures.Angewandte Chemie (International ed. in English) · 2026Article
- Asymmetric Total Synthesis of (-)-Verrucarol.Angewandte Chemie (International ed. in English) · 2026Article
- Halide Bond Assisted Double Desymmetrization of Meso-Dicarboxylic Acids with Symmetrical Olefins via Asymmetric Halogenation.Angewandte Chemie (International ed. in English) · 2026Article
- Synthesis of depressin, cryptomeridiol and 4-Beilstein journal of organic chemistry · 2026Article
- Highly efficient synthesis of the natural product β-himachalene in yeast and its potential as a novel anti-HSV-1 therapeutic agent.Synthetic and systems biotechnology · 2025Article
- Skeletal Editing Strategies Driven by Total Synthesis.Accounts of chemical research · 2025Article
- Optimizing longifolene production inSynthetic and systems biotechnology · 2025Article
- Bioinspired concise synthesis of caged Sesquiterpenoids Artatrovirenols A and B.Nature communications · 2025Article
- Molecular Complexity-Inspired Synthetic Strategies toward the Calyciphylline A-TypeJournal of the American Chemical Society · 2024Article
- C-H functionalization of camphor through emerging approaches.Chemistry letters · 2024Review
- Biocatalytic stereocontrolled head-to-tail cyclizations of unbiased terpenes as a tool in chemoenzymatic synthesis.Nature communications · 2024Article
- Late-stage benzenoid-to-troponoid skeletal modification of the cephalotanes exemplified by the total synthesis of harringtonolide.Nature communications · 2024Article
- Navigating Excess Complexity: Total Synthesis of Daphenylline.Journal of the American Chemical Society · 2024Article
- Mechanistic Investigation of the Rhodium-Catalyzed Transfer Hydroarylation Reaction Involving Reversible C-C Bond Activation.Journal of the American Chemical Society · 2023Article
- Natural Product Synthesis: The Endless Quest for Unreachable Perfection.ACS organic & inorganic Au · 2023Review
- Strategic application of C-H oxidation in natural product total synthesis.Nature reviews. Chemistry · 2023Review
- Highly Enantioselective Catalytic Lactonization at Nonactivated Primary and SecondaryJournal of the American Chemical Society · 2023Article
- Skeletal diversification by C-C cleavage to access bicyclic frameworks from a common tricyclooctane intermediate.Chemical communications (Cambridge, England) · 2023Article
- Photocatalytic Alkylation of C(spAngewandte Chemie (International ed. in English) · 2023Article
- General Synthetic Approach to Diverse Taxane Cores.Journal of the American Chemical Society · 2022Article
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3 authors.
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Abstract
Natural product total synthesis inspires the development of synthesis strategies to access important classes of molecules. In the 1960s, Corey and coworkers demonstrated a visionary preparation of the terpenoid longifolene, using 'strategic bond analysis' to craft a synthesis route. This approach proposes that efficient synthesis routes to bridged, polycyclic structures should be formulated to introduce the bulk of the target's topological complexity at a late stage. Subsequently, similar strategies have proved general for the syntheses of a wide variety of bridged, polycyclic molecules. Here, we demonstrate that an orthogonal strategy where topological complexity is introduced at the outset leads to the short synthesis of the longifolene-related terpenoid longiborneol. To implement this strategy, we access a bicyclo[2.2.1] starting material through scaffold remodelling of readily available (S)-carvone. We also employ a variety of late-stage C-H functionalization tactics in divergent syntheses of many longiborneol congeners. Our strategy may prove effective for the preparation of other topologically complex natural products that contain the bicyclo[2.2.1] framework.
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