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

Abstract

The partial syntheses of two trichothecenes, calonectrin (1)(4β,15-diacetoxy-12, 13-epoxytrichothec-9-ene) and deoxynivalenol (2)(3α,7α,15-trihydroxy-12, 13-epoxytrichothec-9-ene), from a readily available trichothecene, anguidine (3)(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-triacetoxy-12, 13-epi-epoxytrichothec-9-ene (31), of the first semisynthetic trichothecene epi-epoxides, has been prepared and its X-ray crystal structure determined. In significant contrast to its natural isomer (10), epi-epoxide (31) proved to be biologically inactive.