ArticleJournal of the American Chemical Society2018
Total Synthesis of (-)-Xylogranatopyridine B via a Palladium-Catalyzed Oxidative Stannylation of Enones.
Article in Journal of the American Chemical Society, 2018. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 17 papers.
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Who cites it
17 citing papers in PubMed.
- Synthesis of diverse terpenoid frameworks via enzyme-enabled abiotic scaffold hop.Nature chemistry · 2025Article
- A convergent synthetic approach to the tetracyclic core framework of khayanolide-type limonoids.Beilstein journal of organic chemistry · 2025Article
- One-Pot Sequential Synthesis of Alkenylated Dihydroquinolinones and Hexahydroacridinones in Deep Eutectic Solvent Medium.ACS omega · 2024Article
- Uracil-Cu(i) catalyst: allylation of cyclopropanols with Morita-Baylis-Hillman alcohols under water-tolerant conditions.Chemical science · 2024Article
- The Reduction of Carbonyl Compounds with Dicyclopentylzinc: A New Example of Asymmetric Amplifying Autocatalysis.International journal of molecular sciences · 2023Article
- Simmons-Smith Cyclopropanation: A Multifaceted Synthetic Protocol toward the Synthesis of Natural Products and Drugs: A Review.Molecules (Basel, Switzerland) · 2023Review
- 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
- Synthesis of Pyrroles via Consecutive 6π-Electrocyclization/Ring-Contraction of Sulfilimines.Journal of the American Chemical Society · 2021Article
- Dehydrogenative Pd and Ni Catalysis for Total Synthesis.Accounts of chemical research · 2021Review
- Total Synthesis ofOrganic letters · 2021Article
- Total synthesis of dimericChemical science · 2020Article
- Total Synthesis of (+)-Granatumine A and Related Bislactone Limonoid Alkaloids via a Pyran to Pyridine Interconversion.Journal of the American Chemical Society · 2019Article
- Allyl-Nickel Catalysis Enables Carbonyl Dehydrogenation and Oxidative Cycloalkenylation of Ketones.Journal of the American Chemical Society · 2019Article
- Computational and Synthetic Investigation of Cationic Rearrangement in the Putative Biosynthesis of Justicane Triterpenoids.Angewandte Chemie (International ed. in English) · 2019Article
- Chemoselective α,β-Dehydrogenation of Saturated Amides.Angewandte Chemie (International ed. in English) · 2019Article
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4 authors.
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Abstract
We report a total synthesis of the pyridine-containing limonoid alkaloid (-)-xylogranatopyridine B in 11 steps from commercially available dihydrocarvone. The central pyridine ring was assembled by a late-stage fragment coupling approach employing a modified Liebeskind pyridine synthesis. One fragment was prepared by an allyl-palladium catalyzed oxidative enone β-stannylation, in which the key bimetallic β-stannyl palladium enolate intermediate undergoes a β-hydride elimination. This methodology also allowed introduction of alkyl and silyl groups to the β-position of enones.
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