14287-83-3Relevant academic research and scientific papers
Phytotoxic Compounds Produced by Fusarium equiseti. Part 7. Reactions and Rearrangement of the 7-Hydroxy-12,13-epoxytrichothec-9-en-8-one Skeleton
Grove, John Frederick
, p. 1731 - 1736 (2007/10/02)
7α,15-Dihydroxy-12,13-epoxytrichothec-9-en-8-ones, e.g. nivalenol and vomitoxin, rearrange under mild basic conditions to the isomeric 7,13-epoxy-A-nortrichothecane-7-carboxylic acid 15-lactones.With hydrogen chloride, normal addition to the 12,13-epoxide of these compounds occurs, with retention of configuration at C-12, and the more usual rearrangement to the 2β-chloroaprotrichothec-9-en-8-one skeleton is not seen.Catalytic hydrogenation of diacetylnivalenol takes place from the β-face to give correspoding (9R)-trichothecan-8-one.Reliable procedures for the preparation of vomotoxin and nivalenol from their acetates are outlined.
