ArticleJournal of the American Chemical Society2019
Total Synthesis of (+)-Granatumine A and Related Bislactone Limonoid Alkaloids via a Pyran to Pyridine Interconversion.
Article in Journal of the American Chemical Society, 2019. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 16 papers.
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16 citing papers in PubMed, 62 citations in OpenAlex.
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- Synthesis of diverse terpenoid frameworks via enzyme-enabled abiotic scaffold hop.Nature chemistry · 2025Article
- Advancing Total Synthesis Through Skeletal Editing.Accounts of chemical research · 2025Article
- Recent Progress on Natural α-Glucosidase Inhibitors Derived from the Plants and Microorganisms.Current medicinal chemistry · 2025Review
- A convergent synthetic approach to the tetracyclic core framework of khayanolide-type limonoids.Beilstein journal of organic chemistry · 2025Article
- The Cytochalasins and Polyketides from a Mangrove Endophytic FungusMarine drugs · 2024Article
- A Novel Analog of the Natural Product Fraxinellone Protects against Endogenous and Exogenous Neurotoxicants.ACS chemical neuroscience · 2024Article
- UV light-driven late-stage skeletal reorganization to diverse limonoid frameworks: A proof of concept for photobiosynthesis.Science advances · 2023Article
- Article
- Synthesis of (-)-melazolide B, a degraded limonoid, from a natural terpene precursor.Tetrahedron chem · 2022Article
- Dehydrogenative Pd and Ni Catalysis for Total Synthesis.Accounts of chemical research · 2021Review
- Enantioselective Total Synthesis of Andrographolide and 14-Hydroxy-Colladonin: Carbonyl Reductive Coupling and trans-Decalin Formation by Hydrogen Transfer.Angewandte Chemie (International ed. in English) · 2020Article
- Novel biocompatible core/shell FeRSC advances · 2020Article
- Synthesis of Degraded Limonoid Analogs as New Antibacterial Scaffolds againstAntibiotics (Basel, Switzerland) · 2020Article
- Article
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Authors and funding
4 authors at 1 institution in 1 country.
Funding
Abstract
We report the first total synthesis of (+)-granatumine A, a limonoid alkaloid with PTP1B inhibitory activity, in ten steps. Over the course of this study, two key methodological advances were made: a cost-effective procedure for ketone α,β-dehydrogenation using allyl-Pd catalysis, and a Pd-catalyzed protocol to convert epoxyketones to 1,3-diketones. The central tetrasubstituted pyridine is formed by a convergent Knoevenagel condensation and carbonyl-selective electrocyclization cascade, which was followed by a direct transformation of a 2 H-pyran to a pyridine. These studies have led to the structural revision of two members of this family.
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