51550-28-8Relevant academic research and scientific papers
Trichothecene mycotoxin interconversions: Partial syntheses of calonectrin and deoxynivalenol, and of a trichothecene epi-epoxide, 3α,4β,15-triacetoxy-12,13-epi-epoxytrichothec-9-ene
Cameron,Colvin
, p. 887 - 895 (2007/10/02)
The partial syntheses of two trichothecenes, calonectrin (4β,15-diacetoxy-12,13-epoxytrichothec-9-ene) and deoxynivalenol (3α,7α,15-trihydroxy-12,13-epoxytrichothec-9-ene), from a readily available trichothecene, anguidine (4β,15-diacetoxy-3α-hydroxy-12,13-epoxytrichothec-9-ene) are described. In addition, and in order to provide further insight into the mode of action of the trichothecene mycotoxins, 3α,4β,15-tricetoxy-12,13-epi-epoxytrichothec-9-ene, of the first semisynthetic trichothecene epi-epoxides, has been prepared and its X-ray crystal structure determined. In significant contrast to its natural isomer, epi-epoxide proved to be biologically inactive.
Chemical Deoxygenation of the Trichothecenes Diacetoxyscirpenol and Deoxynivalenol
Cameron, Stuart,Colvin, Ernest W.
, p. 365 - 370 (2007/10/02)
Based on a model study using the bicyclooctane epoxy acetates (14) and (15), an efficient one-step procedure for the selective removal of the 12,13-epoxide ring of the trichothecene mycotoxins diacetoxyscirpenol (1; R=H) and deoxynivalenol (2; R=H) has been devised.The key to success proved to be use of the lower-valent tungsten deoxygenation system of Sharpless et al.
Chemical Deoxygenation of the Trichothecenes, Diacetoxyscirpenol and Deoxynivalenol
Colvin, Ernest W.,Cameron, Stuart
, p. 1084 - 1085 (2007/10/02)
Based on a model study using the bicyclic epoxides (9) and (10), an efficient one-step procedure for the selective removal of the 12,13-epoxide ring of the trichothecene toxins has been devised.
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.
Chemical deoxygenation of the epoxide moiety in deoxynivalenol (vomitoxin)
King, Russell R.,Greenhalgh, Roy
, p. 1089 - 1092 (2007/10/02)
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.
