The structure of hildecarpin, an insect antifeedant 6a-hydroxypterocarpan from the roots of Tephrosia hildebrandtii Vatke
Bentley, M. D.
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The structure of hildecarpin, an insect antifeedant 6a-hydroxypterocarpan isolated from the roots of Tephrosia hildebrandtii has been confirmed by a combination of degradation reactions, NMR and mass spectra. Hildecarpin has been dehydrated to the corresponding pterocarpene 3-hydroxy-2-methoxy-8,9-methylenedioxypterocarpene. Hydrogenation and hydrogenolysis of the pterocarpene has afforded the isoflavan 2′, 7-dihydroxy-6-methoxy-4′,5′-methylenedioxyisoflavan, acetylation of which has led to 2′, 7-diacet6xy-6-methoxy-4′,5′-methylenedioxyisoflavan. The NMR and mass spectra of the degradation products confirm the structure previously assigned to hildecarpin.