Die Konstitution von Tanghinin Glykoside und Aglykone, 268. Mitteilung

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Abstract
Degradation of tanghinigenin 9 yields the known methyl 3‐oxo‐7,8β‐epoxy‐14β‐hydroxy‐5β‐etianate 13. This ester, after bromination followed by dehydrobromination with concomitant opening of the oxirane ring, gave methyl 3‐oxo‐8β, 14β‐dihydroxy‐etia‐4,6‐dienate 18. This same compound was obtained from scillirosidin, whose structure has already been established, following an unequivocal route. The dienone 18 from tanghinigenin gave after hydrogenation the two saturated methyl 3‐oxo‐8β, 14β,‐dihydroxy‐etianates 21 and 22, isomeric in the 5‐position. Both these compounds were products of degradation reactions carried out on scillirosidin. Together with earlier results these transformations establish the structure of tanghinigenin as 3β, 14β‐dihydroxy‐7, 8β‐epoxy‐Δ20(22)‐cardenolide 9.

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