ArticleScience (New York, N.Y.)2016
A 15-step synthesis of (+)-ryanodol.
Article in Science (New York, N.Y.), 2016. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 35 papers.
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Who cites it
35 citing papers in PubMed.
- NiH-Catalyzed Enantioconvergent α-Alkenylation of Carbonyl Compounds via Markovnikov Alkyne Hydronickellation.Angewandte Chemie (International ed. in English) · 2026Article
- Terpenes as Naturally Occurring Stereochemical Templates: Conformationally Driven Discovery of Reactivity.Organic letters · 2025Article
- Ligand Design Enables the Palladium-Catalyzed Intermolecular Carbochlorocarbonylation of Alkynes and Cyclopentenone Formation.Journal of the American Chemical Society · 2025Article
- Stereoselective transition metal-catalyzed [(2+2)+1] and [(2+2)+2] carbocyclization reactions using 1,6-enynes with 1,1-disubstituted olefins: construction of quaternary centers.Chemical science · 2025Review
- Stereo-Differentiating Asymmetric Rh(I)-Catalyzed Pauson-Khand Reaction: A DFT-Informed Approach to Thapsigargin Stereoisomers.Journal of the American Chemical Society · 2025Article
- Total syntheses of highly oxidativeBeilstein journal of organic chemistry · 2025Review
- Molecular complexity as a driving force for the advancement of organic synthesis.Nature reviews. Chemistry · 2024Review
- Baeyer-Villiger oxidation: a promising tool for the synthesis of natural products: a review.RSC advances · 2024Review
- Exploring the synthetic potential of epoxide ring opening reactions toward the synthesis of alkaloids and terpenoids: a review.RSC advances · 2024Review
- Climbing the Oxidase Phase Ladder by Using Dioxygen as the Sole Oxidant: The Case Study of Costunolide.Organic letters · 2024Article
- Palladium-Catalyzed Carbonylations: Application in Complex Natural Product Total Synthesis and Recent Developments.The Journal of organic chemistry · 2023Review
- Photoredox catalysis harvesting multiple photon or electrochemical energies.Beilstein journal of organic chemistry · 2023Review
- Synthesis of cis-thiiranes as diastereoselective access to epoxide congeners via 4π-electrocyclization of thiocarbonyl ylides.Nature communications · 2022Article
- Application of Pauson-Khand reaction in the total synthesis of terpenes.RSC advances · 2021Review
- Electrochemical Activation of Diverse Conventional Photoredox Catalysts Induces Potent Photoreductant Activity*.Angewandte Chemie (International ed. in English) · 2021Article
- Synthesis of Complex Diterpenes: Strategies Guided by Oxidation Pattern Analysis.Accounts of chemical research · 2021Article
- Article
- Synthetic, Mechanistic, and Biological Interrogation ofJournal of the American Chemical Society · 2020Article
- Synthesis of Anhydroryanodol.Journal of the American Chemical Society · 2020Article
- Potent Reductants via Electron-Primed Photoredox Catalysis: Unlocking Aryl Chlorides for Radical Coupling.Journal of the American Chemical Society · 2020Article
Corrections and comments
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Authors and funding
3 authors.
Funding
Abstract
(+)-Ryanodine and (+)-ryanodol are complex diterpenoids that modulate intracellular calcium-ion release at ryanodine receptors, ion channels critical for skeletal and cardiac muscle excitation-contraction coupling and synaptic transmission. Chemical derivatization of these diterpenoids has demonstrated that certain peripheral structural modifications can alter binding affinity and selectivity among ryanodine receptor isoforms. Here, we report a short chemical synthesis of (+)-ryanodol that proceeds in only 15 steps from the commercially available terpene (S)-pulegone. The efficiency of the synthesis derives from the use of a Pauson-Khand reaction to rapidly build the carbon framework and a SeO2-mediated oxidation to install three oxygen atoms in a single step. This work highlights how strategic C-O bond constructions can streamline the synthesis of polyhydroxylated terpenes by minimizing protecting group and redox adjustments.
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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.