Xanthones

Bräse, Stefan; Gläser, Franziska; Kramer, Carsten S.; Lindner, Stephanie; Linsenmeier, Anna M.; Masters, Kye-Simeon; Meister, Anne C.; Ruff, Bettina M.; Zhong, Sabilla

doi:10.1007/978-3-7091-1312-7_13

The Chemistry of Mycotoxins

2012

DOI: 10.1007/978-3-7091-1312-7_13

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Xanthones

Stefan Bräse

Franziska Gläser

Carsten S. Kramer

et al.

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Cited by 2 publications

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“…The construction of tetrahydroxanthone natural products and related benzopyranones has relied predominantly on domino aldol-oxa-Michael or Dieckmann cyclization approaches . The current state of the art approaches typically require multiple steps to build the tricyclic core structure, and few catalytic enantioselective examples have been reported .…”

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confidence: 99%

Enantioselective Access to Tetrahydroxanthones via Copper-bis(oxazoline)-Catalyzed [4 + 2] Cycloaddition

et al. 2023

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Highly enantioselective access to tetrahydroxanthone compounds was achieved through copper-bis(oxazoline)-catalyzed [4 + 2] cycloaddition of chrom-4-one dienophiles and Danishefsky’s diene. Oxo-dihydroxanthone (enone) adducts, containing a quaternary stereocenter, are generated in up to 98% yield and 89% ee. Cycloadducts are utilized in the synthesis of tetrahydroxanthones, featuring a novel organotin-mediated quasi-Krapcho decarboxylation of β-keto esters, with retention of stereochemistry. Tetrahydroxanthone is a versatile intermediate to a diverse array of biologically relevant, saturated xanthones.

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Enantioselective Access to Tetrahydroxanthones via Copper-bis(oxazoline)-Catalyzed [4 + 2] Cycloaddition

et al. 2023

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Natural Compounds with Oxepinochromene Scaffold. Structure, Source, Biological Activity and Synthesis

Gašparová

2022

Chemistry & Biodiversity

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Natural products containing oxepinochromene motifs were first isolated from natural sources in 1960s. Natural oxepinochromenes are relatively rare and their source is limited to several endophytic and endolichenic fungi or higher plants. The importance of natural oxepinochromene derivatives lies in their promising biological activity. They exhibit a wide range of activities such as antibacterial, anticancer, anti-inflammatory or antifungal. Consequently, their synthesis has attracted significant interest. This review discusses the source, biosynthesis, biological activity, reactions as well as the total synthesis of oxepinochromene derivatives, belonging to the xanthone, terpenoid and flavone groups of phenolic secondary metabolites.

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Xanthones

Cited by 2 publications

References 124 publications

Enantioselective Access to Tetrahydroxanthones via Copper-bis(oxazoline)-Catalyzed [4 + 2] Cycloaddition

Enantioselective Access to Tetrahydroxanthones via Copper-bis(oxazoline)-Catalyzed [4 + 2] Cycloaddition

Natural Compounds with Oxepinochromene Scaffold. Structure, Source, Biological Activity and Synthesis

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