ArticleNature communications2020
Site-selective C-H hydroxylation of pentacyclic triterpenoids directed by transient chiral pyridine-imino groups.
Article in Nature communications, 2020. 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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11 citing papers in PubMed, 36 citations in OpenAlex.
- Exploring bacterial cytochrome P450s for selective activation of aliphatic C-H bonds in pentacyclic triterpenoids.Nature chemistry · 2026Article
- Article
- The Role of Pentacyclic Triterpenoids in Non-Small Cell Lung Cancer: The Mechanisms of Action and Therapeutic Potential.Pharmaceutics · 2024Review
- Expanding the Clip-and-Cleave Concept: Approaching Enantioselective C-H Hydroxylations by Copper Imine Complexes Using OJournal of the American Chemical Society · 2024Article
- Synthesis of Quillaic Acid through Sustainable C-H Bond Activations.The Journal of organic chemistry · 2024Article
- Regioselective Hydroxylation of Unsymmetrical Ketones Using Cu, HThe Journal of organic chemistry · 2024Article
- Article
- Stereoselective Epoxidation of Triterpenic Allylic Alcohols and Cytotoxicity Evaluation of Synthesized Compounds.Molecules (Basel, Switzerland) · 2023Article
- Oxidative Cleavage of Glycosidic Bonds by Synthetic Mimics of Lytic Polysaccharide Monooxygenases.Organic letters · 2022Article
- Atroposelective Desymmetrization of Resorcinol-Bearing Quinazolinones via Cu-Catalyzed C-O Bond Formation.Organic letters · 2022Article
- Facile Synthesis of Saikosaponins.Molecules (Basel, Switzerland) · 2021Article
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Authors and funding
4 authors at 1 institution in 1 country.
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No grant is acknowledged in the PubMed record.
Abstract
Pentacyclic triterpenoids (PTs) constitute one of the biggest families of natural products, many with higher oxidation state at the D/E rings possess a wide spectrum of biological activties but are poorly accessible. Here we report a site-selective C-H hydroxylation at the D/E rings of PTs paving a way toward these important natural products. We find that Schönecker and Baran's Cu-mediated aerobic oxidation can be applied and become site-selective on PT skeletons, as being effected unexpectedly by the chirality of the transient pyridine-imino directing groups. To prove the applicability, starting from the most abundant triterpenoid feedstock oleanane, three representative saponins bearing hydroxyl groups at C16 or C22 are expeditiously synthesized, and barringtogenol C which bears hydroxyl groups at C16, C21, and C22 is synthesized via a sequential hydroxylation as the key steps.
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