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Search for "resorcylic lactones" in Full Text gives 1 result(s) in Beilstein Journal of Organic Chemistry.

Natural resorcylic lactones derived from alternariol

Joachim Podlech

Beilstein J. Org. Chem. 2024, 20, 2171–2207, doi:10.3762/bjoc.20.187

Joachim Podlech Karlsruhe Institute of Technology (KIT), Institute of Organic Chemistry, Kaiserstraße 12, 76131 Karlsruhe, Germany 10.3762/bjoc.20.187 Abstract In this overview, naturally occurring resorcylic lactones biosynthetically derived from alternariol and almost exclusively produced by

interesting biological activities. Keywords: biosynthesis; fungal metabolites; polyketides; resorcylic lactones; total synthesis; Introduction Alternariol and some of its derivatives are ubiquitous as fungal metabolites present in infested plants and in food and feed, but similarly in soil, in wallpapers

. Derivatives formed through metabolization in the human body (or in animals) are only covered if the respective metabolites were similarly identified as natural products. A thorough survey of the literature revealed (at now) 127 natural products to be classified as natural resorcylic lactones derived from

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Graphical Abstract

Figure 1: Examples of compounds covered in this review categorized in six sub-classes (see text).

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Figure 2: Examples of compounds not covered in this review.

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Figure 3: Wrongly assigned and thus obsolete structures (details will be discussed in the respective chapters...

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Figure 4: Alternariol with the correct IUPAC numbering and an occasionally used numbering based on the biphen...

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Figure 5: Alternariol O-methyl ethers.

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Figure 6: Alternariol O-glycosides.

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Figure 7: Alternariol O-acetates and O-sulfates.

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Figure 8: 2-Hydroxy- and 4-hydroxy-substituted alternariol and its O-methyl ethers.

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Figure 9: Chloro- and amino-substituted alternariol and its O-methyl ethers.

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Figure 10: Presumed alternariol derivatives with non-canonical substitution pattern.

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Figure 11: Alternariol derivatives with the 1-methyl group hydroxylated.

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Figure 12: Verrulactones: pseudo-dimeric derivatives of altertenuol and related compounds.

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Figure 13: Biaryls formed by reductive lactone opening and/or by decarboxylation.

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Figure 14: Altenuene and its diastereomers.

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Figure 15: 9-O-Demethylated altenuene diastereomers.

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Figure 16: Acetylated and methylated altenuene diastereomers.

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Figure 17: Altenuene diastereomers modified with lactic acid, pyruvic acid, or acetone.

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Figure 18: Neoaltenuene and related compounds.

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Figure 19: Dehydroaltenusin and its derivatives.

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Scheme 1: Equilibrium of dehydroaltenusin in polar solvents [278].

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Figure 20: Further quinoid derivatives.

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Figure 21: Dehydroaltenuenes.

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Figure 22: Complex aggregates containing dehydroaltenuene substructures and related compounds.

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Figure 23: Dihydroaltenuenes.

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Figure 24: Altenuic acids and related compounds.

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Figure 25: Cyclopentane- and cyclopentene-fused derivatives.

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Figure 26: Cyclopentenone-fused derivatives.

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Figure 27: Spiro-fused derivatives and a related ring-opened derivative.

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Figure 28: Lactones-fused and lactone-substituted derivatives.

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Scheme 2: Biosynthesis of alternariol [324].

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Scheme 3: Biosynthesis of alternariol and its immediate successors with the genes involved in the respective ...

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Scheme 4: Presumed formation of altenuene and its diastereomers and of botrallin.

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Scheme 5: Presumed formation of altenuic acids and related compounds.

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Scheme 6: A selection of plausible biosynthetic paths to cyclopenta-fused metabolites. (No stereochemistry is...

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Scheme 7: Biomimetic synthesis of alternariol (1) by Harris and Hay [66].

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Scheme 8: Total synthesis of alternariol (1) by Subba Rao et al. using a Diels–Alder approach [34].

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Scheme 9: Total synthesis of alternariol (1) using a Suzuki strategy by Koch and Podlech [62], improved by Kim et...

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Scheme 10: Total synthesis of alternariol (1) using an intramolecular biaryl coupling by Abe et al. [63].

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Scheme 11: Total synthesis of altenuene (54) and isoaltenuene (55) by Podlech et al. [249].

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Scheme 12: Total synthesis of neoaltenuene (69) by Podlech et al. [35].

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Scheme 13: Total synthesis of TMC-264 (79) by Tatsuta et al. [185].

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Scheme 14: Total synthesis of cephalosol (99) by Koert et al. [304].

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Published 30 Aug 2024

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