Evodia elleryana

Hydroxydictamnine, described as 7-O-demethylevolitrine, was isolated first from Evodia elleryana F. Muell (139) it was later obtained from Melicope confusa (Mesr.) Liu and named confusameline (132). The structure was established by conversion with diazomethane into 7-methoxy-dictamnine (evolitrine). 

Evodia elleryana also contains evellerine (165), a derivative of 7-hy-droxydictamnine. Evellerine was shown to be a 4-methoxyfuroquinoline by conversion into the isoalkaloid isoevellerine (166) by heating with methyl iodide. Isoevellerine furnished a monoacetyl derivative, and yielded 7-methoxyisodictamnine when heated with sodium hydroxide and dimethyl-sulfate. The structure of the side chain in evellerine was established by reaction of isoevellerine with periodate and the identification of acetone... 

Evodione (6) is also a known natural product which had been isolated from Evodia elleryana (9,10). Its structure had been determined by chemical degeneration (II) and total synthesis (12) previously, but there was no H NMR and C NMR spectral data available in literature. To confirm that compound 6 was evodione, isoevodionol (11) was transformed to evodione in two steps of reactions. First, 11 was converted to 11a via Elb reaction (13), then methylation of 11a with (CH3)2S04/K2C03 gave evodione (Figure 4). The spectral data ( H NMR and EIMS) of the synthetic evodione is exactly same to compound 6. 

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