Hypochlorite-promoted transformations of trichothecenes, 3. Deoxynivalenol

Treatment of deoxynivalenol [3] in MeOH with hypochlorite bleach containing added NaOH gave rise to a single major product, the 9 alpha, 10 alpha, 12 beta, 13 beta-diepoxy-8,15-hemiketal 4. Thus, the reaction followed a very different course from that observed for verrucarol [2], where rearrangement involving opening of the starting 12,13-epoxide and a haloform-like oxidation took place.