Synthesis
DOI: 10.1055/a-1698-8328
paper
SYNTHESIS Conference Special Issue ISySyCat21

Concise Syntheses of Alternariol, Alternariol-9-monomethyl Ether and Their D3-Isotopologues

a  HPC Standards GmbH, Am Wieseneck 7, 04451 Cunnersdorf, Germany
,
Julian Gebauer
b  AnalytiCon Discovery GmbH, Hermannswerder Haus 17, 14473 Potsdam, Germany
,
Matthias Koch
c  Bundesanstalt für Materialforschung und -prüfung, Abteilung Analytische Chemie, Referenzmaterialien, Richard-Willstätter-Straße 11, 12489 Berlin-Adlershof, Germany
› Author Affiliations
This work is funded by Zentrales Innovationsprogramm Mittelstand (ZIM) of the Bundesministerium für Wirtschaft und Energie (BMWi) (Federal Ministry for Economic Affairs and Energy) (Grant No. 16 KN047802) and the Frankenförder Forschungsgesellschaft.


Abstract

Alternariol (AOH) and alternariol-9-monomethyl ether (AME) are two secondary metabolites of Alternaria fungi which can be found in various foodstuffs like tomatoes, nuts, and grains. Due to their toxicity and potential mutagenic activity the need for the development of high-throughput methods for the supervision of AOH and AME levels is of increasing interest. As the availability of both native and labeled AOH and AME analytical standards is very limited, we herein present a novel and concise approach towards their synthesis by employing a ruthenium-catalyzed ortho-arylation as the key step. Finally, we demonstrate their suitability as internal standards in stable-isotope dilution assay (SIDA)-HPLC-MS/MS analysis, a technique commonly used for the quantification of natural products in food and feed.

Supporting Information



Publication History

Received: 09 September 2021

Accepted after revision: 16 November 2021

Publication Date:
16 November 2021 (online)

© 2021. Thieme. All rights reserved

Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany

 
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