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Keywords = dihydroxycalonectrins

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12 pages, 360 KiB  
Article
Stereoselective Luche Reduction of Deoxynivalenol and Three of Its Acetylated Derivatives at C8
by Philipp Fruhmann, Christian Hametner, Hannes Mikula, Gerhard Adam, Rudolf Krska and Johannes Fröhlich
Toxins 2014, 6(1), 325-336; https://doi.org/10.3390/toxins6010325 - 10 Jan 2014
Cited by 11 | Viewed by 15070
Abstract
The trichothecene mycotoxin deoxynivalenol (DON) is a well known and common contaminant in food and feed. Acetylated derivatives and other biosynthetic precursors can occur together with the main toxin. A key biosynthetic step towards DON involves an oxidation of the 8-OH group of [...] Read more.
The trichothecene mycotoxin deoxynivalenol (DON) is a well known and common contaminant in food and feed. Acetylated derivatives and other biosynthetic precursors can occur together with the main toxin. A key biosynthetic step towards DON involves an oxidation of the 8-OH group of 7,8-dihydroxycalonectrin. Since analytical standards for the intermediates are not available and these intermediates are therefore rarely studied, we aimed for a synthetic method to invert this reaction, making a series of calonectrin-derived precursors accessible. We did this by developing an efficient protocol for stereoselective Luche reduction at C8. This method was used to access 3,7,8,15-tetrahydroxyscirpene, 3-deacetyl-7,8-dihydroxycalonectrin, 15-deacetyl-7,8-dihydroxycalonectrin and 7,8-dihydroxycalonectrin, which were characterized using several NMR techniques. Beside the development of a method which could basically be used for all type B trichothecenes, we opened a synthetic route towards different acetylated calonectrins. Full article
(This article belongs to the Special Issue Recent Advances and Perspectives in Deoxynivalenol Research)
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