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

作者：Fruhmann Philipp^*; Hametner Christian; Mikula Hannes; Adam Gerhard; Krska Rudolf; Froehlich Johannes

来源：Toxins, 2014, 6(1): 325-336.

DOI：10.3390/toxins6010325

• dihydroxycalonectrins
• trichothecenes
• DON
• Luche reduction
• scirpene

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.

• 出版日期2014-1