Total synthesis of masked Alternaria mycotoxins—sulfates and glucosides of alternariol (AOH) and alternariol-9-methyl ether (AME)

The synthesis of different protected alternariol derivatives using intramolecular cyclization of iodoresorcylic acid phenyl esters by palladium-catalyzed C–H activation as key step is presented. Furthermore, chemical sulfation and glucosylation were applied for the preparation of conjugated Alternar...

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Bibliographic Details
Published in:Tetrahedron 2013-12, Vol.69 (48), p.10322-10330
Main Authors: Mikula, Hannes, Skrinjar, Philipp, Sohr, Barbara, Ellmer, Doris, Hametner, Christian, Fröhlich, Johannes
Format: Article
Language:English
Subjects:
Alternaria
Alternaria toxins
Alternariol
Conjugates
Derivatives
Esters
Ethers
Glycosylation
Masked mycotoxins
Metabolism
Mycotoxins
Sulfation
Synthesis
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Summary:The synthesis of different protected alternariol derivatives using intramolecular cyclization of iodoresorcylic acid phenyl esters by palladium-catalyzed C–H activation as key step is presented. Furthermore, chemical sulfation and glucosylation were applied for the preparation of conjugated Alternaria mycotoxins. These compounds are suspected to be formed during metabolism in contaminated plants. Therefore, all synthetic conjugates prepared within this work serve as reference materials for further studies in the fields of bioanalytics and toxicology of mycotoxins. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2013.10.008