Phytotoxic Compound Produced by Fusarium equiseti. Part 8. Acid Catalysed Rearrangement of 12,13-Epoxytrichothec-9-enes
The acid catalysed rearrangement of 12,13-epoxytrichothec-9-enes to give biologically inactive 10,13-cyclotrichothecane or apotrichothec-9-ene products depends on the substitution pattern of both rings A and C.The former rearrangement is adversely affected by 8α-substitution and by the presence of a 4,15-macrolide ring; the latter rearrangement by 7α- and by 3α-substitution.Compared with the trichothecene, the greater flexibility of the apotrichothecene skeleton is reflected in the range of values for the ring C vicinal coupling constants in the 1H n.m.r. spectra.
Grove, John Frederick
p. 647 - 654
(2007/10/02)
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