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.

中文翻译：

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Alternariol、Alternariol-9-monomethyl Ether 及其 D3-Isotopologues 的简明合成

Alternariol (AOH) 和alternariol-9-monomethyl ether (AME) 是链格孢真菌的两种次级代谢产物，可以在西红柿、坚果和谷物等各种食品中找到。由于它们的毒性和潜在的诱变活性，开发用于监测 AOH 和 AME 水平的高通量方法的需求越来越受到关注。由于天然和标记的 AOH 和 AME 分析标准的可用性非常有限，我们在此提出了一种新颖而简洁的合成方法，采用钌催化的邻芳基化作为关键步骤。最后，我们证明了它们在稳定同位素稀释测定 (SIDA)-HPLC-MS/MS 分析中作为内标的适用性，这是一种常用于定量食品和饲料中天然产物的技术。