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.
Burrows
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U.S. Army Biomedical Research & Development Laboratory, Fort Detrick, Frederick, Maryland 21701-5010.
Szafraniec
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D055598:Chemical Phenomena; D002621:Chemistry; D006997:Hypochlorous Acid; D009682:Magnetic Resonance Spectroscopy; D012717:Sesquiterpenes / Q000032:analysis*; D014255:Trichothecenes / Q000032:analysis*
D012717:Sesquiterpenes; D014255:Trichothecenes; D006997:Hypochlorous Acid; C007262:deoxynivalenol