ArticleJournal of the American Chemical Society2022
Strategy Evolution in a Skeletal Remodeling and C-H Functionalization-Based Synthesis of the Longiborneol Sesquiterpenoids.
Article in Journal of the American Chemical Society, 2022. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 10 papers.
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10 citing papers in PubMed, 29 citations in OpenAlex.
- Halide Bond Assisted Double Desymmetrization of Meso-Dicarboxylic Acids with Symmetrical Olefins via Asymmetric Halogenation.Angewandte Chemie (International ed. in English) · 2026Article
- Article
- Skeletal Editing Strategies Driven by Total Synthesis.Accounts of chemical research · 2025Article
- Bioinspired concise synthesis of caged Sesquiterpenoids Artatrovirenols A and B.Nature communications · 2025Article
- C-H functionalization of camphor through emerging approaches.Chemistry letters · 2024Review
- Directed Hydrogen Atom Transfer for Selective Reactions of Polyenols.Journal of the American Chemical Society · 2024Article
- Late-stage benzenoid-to-troponoid skeletal modification of the cephalotanes exemplified by the total synthesis of harringtonolide.Nature communications · 2024Article
- 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
- Carboxylic Acid Directed γ-Lactonization of Unactivated Primary C-H Bonds Catalyzed by Mn Complexes: Application to Stereoselective Natural Product Diversification.Journal of the American Chemical Society · 2022Article
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3 authors at 2 institutions in 2 countries.
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Abstract
Detailed herein are our synthesis studies of longiborneol and related natural products. Our overarching goals of utilizing a "camphor first" strategy enabled by skeletal remodeling of carvone, and late-stage diversification using C-H functionalizations, led to divergent syntheses of the target natural products. Our initial approach proposed a lithiate addition to unite two fragments followed by a Conia-ene or Pd-mediated cycloalkylation reaction sequence to install the seven-membered ring emblematic of the longibornane core. This approach was unsuccessful and evolved into a revised plan that employed a Wittig coupling and a radical cyclization to establish the core. A reductive radical cyclization, which was explored first, led to a synthesis of copaborneol, a structural isomer of longiborneol. Alternatively, a metal-hydride hydrogen atom transfer-initiated cyclization was effective for a synthesis of longiborneol. Late-stage C-H functionalization of the longibornane core led to a number of hydroxylated longiborneol congeners. The need for significant optimization of the strategies that were employed as well as the methods for C-H functionalization to implement these strategies highlights the ongoing challenges in applying these powerful reactions. Nevertheless, the reported approach enables functionalization of every natural product-relevant C-H bond in the longibornane skeleton.
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