Synthesis of three Tricholoma-derived indoles via an ortho-quinone methide

Homer, Joshua A.; Sperry, Jonathan

doi:10.24820/ark.5550190.p010.475

Cited by 4 publications

(3 citation statements)

References 16 publications

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Section: New Alkaloids Found In Mushroom Since 2002mentioning

confidence: 99%

“…5-Methoxy-4methoxymethyl-2-methyl-1H-indole (75, Figure 6) was only found in the volatile components of Tricholoma caligatum, by Fons et al (2006) [48]. Its synthesis was accomplished in two steps and it achieved 17% global yield starting from 5-hydroxy-2-methylindole [114]. Both compounds 64 and 65 have special relevance in therapeutic treatments due to their low toxicity and suitable physiological tolerance [21].…”

Section: Indolesmentioning

confidence: 99%

“…5-Methoxy-4-methoxymethyl-2-methyl-1H-indole (75, Figure 6) was only found in the volatile components of Tricholoma caligatum, by Fons et al (2006) [48]. Its synthesis was accomplished in two steps and it achieved 17% global yield starting from 5-hydroxy-2methylindole [114]. The three N-glucosylated indoles 76-78 (Figure 6) were isolated from the basidiomycete C. brunneus, with 76 and 77 being new compounds [49].…”

Section: Indolesmentioning

confidence: 99%

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Structures and Biological Activities of Alkaloids Produced by Mushrooms, a Fungal Subgroup

Zorrilla

Evidente

2022

Biomolecules

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Alkaloids are a wide family of basic N-containing natural products, whose research has revealed bioactive compounds of pharmacological interest. Studies on these compounds have focused more attention on those produced by plants, although other types of organisms have also been proven to synthesize bioactive alkaloids, such as animals, marine organisms, bacteria, and fungi. This review covers the findings of the last 20 years (2002–2022) related to the isolation, structures, and biological activities of the alkaloids produced by mushrooms, a fungal subgroup, and their potential to develop drugs and agrochemicals. In some cases, the synthesis of the reviewed compounds and structure−activity relationship studies have been described.

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Section: New Alkaloids Found In Mushroom Since 2002mentioning

confidence: 99%

Section: Indolesmentioning

confidence: 99%

Section: Indolesmentioning

confidence: 99%

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Structures and Biological Activities of Alkaloids Produced by Mushrooms, a Fungal Subgroup

Zorrilla

Evidente

2022

Biomolecules

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Biomimetic synthesis of the bisindole framework present in sciodole, an alkaloid fromTricholoma sciodes

Homer

Sperry

2018

Org. Biomol. Chem.

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Alkoxyalkylation of Electron-Rich Aromatic Compounds

Simon,

Lőrinczi,

Szatmári

2024

IJMS

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Alkoxyalkylation and hydroxyalkylation methods utilizing oxo-compound derivatives such as aldehydes, acetals or acetylenes and various alcohols or water are widely used tools in preparative organic chemistry to synthesize bioactive compounds, biosensors, supramolecular compounds and petrochemicals. The syntheses of such molecules of broad relevance are facilitated by acid, base or heterogenous catalysis. However, degradation of the N-analogous Mannich bases are reported to yield alkoxyalkyl derivatives via the retro-Mannich reaction. The mutual derivative of all mentioned species are quinone methides, which are reported to form under both alkoxy- and aminoalkylative conditions and via the degradation of the Mannich-products. The aim of this review is to summarize the alkoxyalkylation (most commonly alkoxymethylation) of electron-rich arenes sorted by the methods of alkoxyalkylation (direct or via retro-Mannich reaction) and the substrate arenes, such as phenolic and derived carbocycles, heterocycles and the widely examined indole derivatives.

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Synthesis of three Tricholoma-derived indoles via an ortho-quinone methide

Cited by 4 publications

References 16 publications

Structures and Biological Activities of Alkaloids Produced by Mushrooms, a Fungal Subgroup

Structures and Biological Activities of Alkaloids Produced by Mushrooms, a Fungal Subgroup

Biomimetic synthesis of the bisindole framework present in sciodole, an alkaloid fromTricholoma sciodes

Alkoxyalkylation of Electron-Rich Aromatic Compounds

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