- Chemical Deoxygenation of the Trichothecenes, Diacetoxyscirpenol and Deoxynivalenol
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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.
- Colvin, Ernest W.,Cameron, Stuart
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- 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
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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.
- Cameron,Colvin
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p. 887 - 895
(2007/10/02)
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- Chemical Deoxygenation of the Trichothecenes Diacetoxyscirpenol and Deoxynivalenol
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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.
- Cameron, Stuart,Colvin, Ernest W.
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p. 365 - 370
(2007/10/02)
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- Synthesis and Biological Evaluation of a Trichothecene epi-Epoxide, 3α,4β,15-Triacetoxy-12,13-epi-epoxytrichothec-9-ene
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In order to provide additional insight into the mode of action of the trichothecene mycotoxins, one of the first semi-synthetic trichothecene epi-epoxides (8) has been prepared; in dramatic contrast to its natural isomer (9), this compound proved tobe devoid of significant biological activity.
- Colvin, Ernest W.,Cameron, Stuart
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p. 1642 - 1643
(2007/10/02)
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