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Stereoselective Luche Reduction of Deoxynivalenol and Three of Its Acetylated Derivatives at C8
AbstractThe 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.
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Fruhmann, P.; Hametner, C.; Mikula, H.; Adam, G.; Krska, R.; Fröhlich, J. Stereoselective Luche Reduction of Deoxynivalenol and Three of Its Acetylated Derivatives at C8. Toxins 2014, 6, 325-336.View more citation formats
Fruhmann P, Hametner C, Mikula H, Adam G, Krska R, Fröhlich J. Stereoselective Luche Reduction of Deoxynivalenol and Three of Its Acetylated Derivatives at C8. Toxins. 2014; 6(1):325-336.Chicago/Turabian Style
Fruhmann, Philipp; Hametner, Christian; Mikula, Hannes; Adam, Gerhard; Krska, Rudolf; Fröhlich, Johannes. 2014. "Stereoselective Luche Reduction of Deoxynivalenol and Three of Its Acetylated Derivatives at C8." Toxins 6, no. 1: 325-336.
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