An 1H nuclear magnetic resonance study of derivatives of 3-hydroxy-12,13-epoxytrichothec-9-enes

Abstract

The 250-MHz 1H nuclear magnetic resonance spectra of 36 natural and synthetic trichothecenes have been analyzed and the chemical shifts as well as the vicinal and long-range coupling constants determined. Knowledge of the 16-CH3 chemical shift enables the substitution pattern of the A ring to be defined. Similarly, oxygenation in the C ring results in easily identifiable resonances. The J2,3 and J3,4 values define the configuration of substituents at C-3 and C-4, while the configuration at C-7 and C-8 can be defined by the J7,8, J7α,11, and J7β,15 values. The trichothecene ring system adopts the most stable A-half-chair, B-chair conformation in solution. The correlations obtained allow easy structural determination of unknown trichothecenes.