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 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.
Keywords: dihydroxycalonectrins; trichothecenes; DON; Luche reduction; scirpene
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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.
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.
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.