Phytotoxic compounds produced by Fusarium equiseti. Part V. Transformation products of 4β,15-diacetoxy-3α,7α-dihydroxy-12,13-epoxytrichothec-9-en-8-one and the structures of nivalenol and fusarenone

Abstract

The absolute configuration of the toxic C₁₉H₂₄O₉ metabolic product of Fusarium scirpi is established as 4β, 15-diacetoxy-3α,7α-dihydroxy-12,13-epoxytrichothec-9-en-8-one (I; R¹= R⁴= H, R²= R³= Ac) by the synthesis of a derivative from a trichothecane of known absolute configuration. Some derivatives and transformation products of the enone (I; R¹= R⁴= H, R²= R³= Ac) are described. Nivalenol, obtained from rice infected with Fusarium nivale, is identical with the parent alcohol (I; R¹= R²= R³= R⁴= H). Fusarenone, from the same source, is the 4β-monoacetate (I; R¹= R²= R⁴= H, R³= Ac).