ArticleAngewandte Chemie (International ed. in English)2022
Total Synthesis and Late-Stage C-H Oxidations of ent-Trachylobane Natural Products.
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 11 papers.
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Who cites it
11 citing papers in PubMed.
- Fluorinated Solvents for Chemoselective Oxidations: A Strategy toward Synthetic Ideality in Natural Product Synthesis.ACS organic & inorganic Au · 2026Article
- Harnessing Photochemistry in Natural Product Synthesis: From Strategy to Applications.Journal of natural products · 2025Review
- Recent Advances in Bioinspired Cu-Directed C-H Hydroxylation Reactions.Accounts of chemical research · 2025Article
- Bio-inspired total synthesis of daphnepapytone A.Chemical science · 2025Article
- Article
- Vinyltriarylbismuthonium Salts: Powerful Vehicles for α-Vinylation of Carbonyl Compounds.Journal of the American Chemical Society · 2024Article
- C-H Functionalization-Enabled 11-Step Semisynthesis of (-)-Veragranine A and Characterization of Synthetic Analogs in Osteoarthritis-related Pain Treatment.Journal of the American Chemical Society · 2024Article
- Catalyst and Medium Control over Rebound Pathways in Manganese-Catalyzed Methylenic C-H Bond Oxidation.Journal of the American Chemical Society · 2024Article
- Total Syntheses of Hosieines A-C.Advanced science (Weinheim, Baden-Wurttemberg, Germany) · 2024Article
- Strategic application of C-H oxidation in natural product total synthesis.Nature reviews. Chemistry · 2023Review
- Total Synthesis and Late-Stage C-H Oxidations of ent-Trachylobane Natural Products.Angewandte Chemie (International ed. in English) · 2022Article
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Authors and funding
3 authors.
Funding
Abstract
Herein, we present our studies to construct seven ent-trachylobane diterpenoids by employing a bioinspired two-phase synthetic strategy. The first phase provided enantioselective and scalable access to five ent-trachylobanes, of which methyl ent-trachyloban-19-oate was produced on a 300 mg scale. During the second phase, chemical C-H oxidation methods were employed to enable selective conversion to two naturally occurring higher functionalized ent-trachylobanes. The formation of regioisomeric analogs, which are currently inaccessible via enzymatic methods, reveals the potential as well as limitations of established chemical C-H oxidation protocols for complex molecule synthesis.
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Registered trials
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.