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Toxins 2014, 6(1), 325-336; doi:10.3390/toxins6010325

Stereoselective Luche Reduction of Deoxynivalenol and Three of Its Acetylated Derivatives at C8

Institute of Applied Synthetic Chemistry, Vienna University of Technology, Getreidemarkt 9, Vienna 1060, Austria
Department of Applied Genetics and Cell Biology, University of Natural Resources and Life Sciences, Vienna (BOKU), Konrad Lorenz Str. 24, Tulln 3430, Austria
Department for Agrobiotechnology (IFA-Tulln), Center for Analytical Chemistry, University of Natural Resources and Life Sciences, Vienna (BOKU), Konrad Lorenz Str. 20, Tulln 3430, Austria
Author to whom correspondence should be addressed.
Received: 6 November 2013 / Revised: 29 December 2013 / Accepted: 31 December 2013 / Published: 10 January 2014
(This article belongs to the Special Issue Recent Advances and Perspectives in Deoxynivalenol Research)
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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. View Full-Text
Keywords: dihydroxycalonectrins; trichothecenes; DON; Luche reduction; scirpene 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.

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