Abstract
Hydrogenation of α-anhydrodihydrocaranine (V) or anhydrocaranine (VII) with Adams catalyst in acetic acid or the Hauptmann reduction of α-dihydrocaranone (XX) yielded (—)γ-lycorane (XVII). Catalytic reduction of β-anhydrodihydrocaranine (IX) with palladium-carbon in ethanol gave (+)γ-lycorane (XVIII), while with Adams catalyst in acetic acid it afforded (+)δ-lycorane (XIX) along with (—)β-lycorane (III). Reduction of anhydrocaranine in ethanol gave (±)γ-lycorane which was also obtained by hydrogenation of anhydrolycorine (X). Based on these findings, the configurational structures of α-, β-, γ- and δ-lycorane were established and the configuration of dihydrolycorine was confirmed.
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