Alkaloids Derived from Dibenzofuran

In contrast to lycoramine, the ether linkage in galanthamine is cleaved by hydrobromic acid to a dibasic phenol, apogalanthamine 

and CXIIo, respectively. 0-0-Dimethylapogalanthamine, identified as its styphnate and methiodide salts, was synthesized in the following manner. 

From these degradation data, two partial formulas for galanthamine, CXIII and CXIV, are possible. Structure CXIV would be preferred if the formation of apogalanthamine could be shown to occur without 

This alkaloid, C17H19NO3, was isolated in low yield from the double narcissi Texas and Irene Copeland (90a). It is reported to contain one methoxyl, one iV -methyl group, and an a,j8-unsaturated ketone function. It is considered to be identical with galanthaminone obtained by the manganese dioxide oxidation of galanthamine. Reduction of narwedine with sodium and amyl alcohol has been reported to give epigalanthamine. 

The frequent occurrence of tazettine in many genera of the Amarylli-daceae has led several groups to attempt the determination of its structure. With one exception (121), these workers have reaffirmed the molecular formula CigHgiNOs for the alkaloid, including a methylene-dioxy group, one methoxyl, one N-methyl, and one hydroxyl. A double 

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Galanthamine-type alkaloids derived from a dibenzofuran ring Crinine-type alkaloids derived from 5,10b-ethanophenanthridine Montanine-type alkaloids derived from 5, 11b-... 

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