Abstract
Reaction of triacetoxydeoxynivalenol (3) with hydrobromic acid–acetic acid at reflux temperatures yielded 3α,7α, 13,15-tetraacetoxy-2-bromo apotrichothec-9-en-8-one (5) and 3α,7α,15-triacetoxy-13-bromo-12-hydroxytrichothec-9-en-8-one (4). Dehalohydrination of the 13,12-bromohydrin derivative with Zn–acetic acid followed by deacetylation with sodium ethoxide gave 3α,7α,15-trihydroxytrichothec-9,12-dien-8-one (2). This compound proved identical to the transformation product isolated from incubation of deoxynivalenol (vomitoxin) in vitro with rumen microorganisms.
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