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. 2017 Jul 31;7:6929. doi: 10.1038/s41598-017-07319-0

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© The Author(s) 2017

Open Access This article is licensed under a Creative Commons Attribution 4.0 International License, which permits use, sharing, adaptation, distribution and reproduction in any medium or format, as long as you give appropriate credit to the original author(s) and the source, provide a link to the Creative Commons license, and indicate if changes were made. The images or other third party material in this article are included in the article’s Creative Commons license, unless indicated otherwise in a credit line to the material. If material is not included in the article’s Creative Commons license and your intended use is not permitted by statutory regulation or exceeds the permitted use, you will need to obtain permission directly from the copyright holder. To view a copy of this license, visit http://creativecommons.org/licenses/by/4.0/.

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The chemical synthesis of 3-keto-DON and the retrieved proton (¹H) NMR spectra of the synthesized compound. (Top): Chemical synthesis of 3-keto-DON (D) encompasses protecting the 7,15-dihydroxyl groups of DON (A) by using 2,2-dimethoxypropane (i) before oxidizing the secondary hydroxyl (ii) in a later phase. The protecting-groups were removed later through a hydrolysis initiated with TFA (iii) to finally obtain the desired 3-keto-DON intermediate (D). (Bottom): The obtained chemical shifts of ¹H-NMR signals of the chemically synthesized 3-keto-DON are identical with previously published data for the same compound^{10, 15}. A detailed discussion of the spectra is found within the results section. An overall yield close to 36% was achieved combined with purity levels close to 95%.