ArticleChemistry, an Asian journal2020
Diastereoselective Synthesis of Benzoxanthenones.
Article in Chemistry, an Asian journal, 2020. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 5 papers.
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Who cites it
5 citing papers in PubMed, 8 citations in OpenAlex.
- Benzoxanthenone Lignans Related to Carpanone, Polemanone, and Sauchinone: Natural Origin, Chemical Syntheses, and Pharmacological Properties.Molecules (Basel, Switzerland) · 2025Review
- Recent advances in oxidative phenol coupling for the total synthesis of natural products.Natural product reports · 2024Review
- Visible-Light-Induced Oxidative Coupling of Phenols and Alkenylphenols with a Recyclable, Solid Photocatalyst.Organic letters · 2023Article
- Catalytic Oxidative Coupling of Phenols and Related Compounds.ACS catalysis · 2022Article
- Oxidative dehydrogenative couplings of alkenyl phenols.Organic & biomolecular chemistry · 2021Review
Corrections and comments
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Authors and funding
2 authors at 1 institution in 1 country.
Funding
Abstract
An oxidative catalytic vanadium(V) system was developed to access the naturally nonabundant diastereomers of carpanone from the corresponding alkenyl phenol monomer in one pot by tandem oxidation, oxidative coupling, and 4+2 cyclization. This system was applied to the synthesis of two other analogues of carpanone. Mild oxidizing silver salts were used as the terminal oxidant to minimize background oxidation which produces the natural diastereomer of carpanone. Further, the first examples of enantioselective oxidative benzoxanthenone formation are reported. Solvent polarity has a strong effect on enantioselectivity, consistent with a mechanism involving binding of vanadium Schiff base catalysts to the alcoholic moiety of the alkenyl phenols during the cyclization step.
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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.