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

Toxins

Philipp Fruhmann²  Christian Hametner²  Hannes Mikula²  Gerhard Adam³  Rudolf Krska¹ 

[1] 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; E-Mail:;Institute of Applied Synthetic Chemistry, Vienna University of Technology, Getreidemarkt 9, Vienna 1060, Austria; E-Mails:;Department of Applied Genetics and Cell Biology, University of Natural Resources and Life Sciences, Vienna (BOKU), Konrad Lorenz Str. 24, Tulln 3430, Austria; E-Mail:

关键词: dihydroxycalonectrins;    trichothecenes;    DON;    Luche reduction;    scirpene;   

DOI  :  10.3390/toxins6010325

来源: mdpi

【 摘 要 】

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.

【 授权许可】

CC BY   
© 2014 by the authors; licensee MDPI, Basel, Switzerland.