Phytotoxic Compounds produced by Fusarium equiseti. Part 11.l The Chemistry of Diacetoxyscirpenol By A. W. Dawkins Diacetoxyscirpenol, the principal toxic metabolic product of Fusarium scirpi, is shown to possess structure ( I a ) by transformation to a derivative ( I I I d ) of verrucarol.
The structures of the 3.4-seco-products from the oxidative fission of trichothecan-3a,4~,15-triols by activated manganese dioxide have been elucidated.THE trans-ap-glycol system in 12,13-epoxytrichothec-9-en-3a,4@,15-triol ( I ; R = R' = H) (scirpentriol: for nomenclature see ref.2) and in the 15-monoacetate (I; R = Ac, R' = H) was shown to be stable to peri-odate314 and to lead tetra-acetate in acetic acid: but was cleaved by the latter reagent in chloroform to give, from the triol (I; R = R' = H), in fair yield, an amorphous hemiacetal (VIII; R = H), characterised as the acetate (VIII; R = Ac). The hemiacetal (VIII; R = H) was oxidised further by chromic oxide in dimethylformamide in the presence of sulphuric acid to an amorphous 8-lactone which was considered to have the structure (VII). Ring c of the trichothecan-3,4-diol 4 €3.
Die Oxidation der Trichothecanderivate (Ia) und (Ib) mit aktiviertem Mangandioxid führt zu den "maskierten" Aldehyden (II) und den Lactonen (III) und (IV); die Dihydroderivate (Va) und (Vb) reagieren analog.
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