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A benzyne type reaction of 1‐bromo‐3,4‐dimethoxybenzene (V) with 3,4‐dihydro‐6,7‐methylenedioxy‐I(2H)naphthalenone (VI) gave the tetralone derivative VII, which was converted into the amine IX via the oxime VIII. A Mannich reaction of IX afforded the benzo[c]phen‐anthridine II which was then transformed into oxynitidine (I) and nitidine (IV).

Alternative total syntheses of galanthamine (Ia) and N-benzyfgalanthamine iodide (VIa) were carried out by phenolic oxidative reactions of the corresponding amides (IIIf and e). Both (-)-and (&)-galanthamine showed analgesic activity comparable to that of morphine. GALANTHAJSINE,~ anAmaryllidaceae alkaloid isolated from Lycoris ~adiata,~.* was assigned structure (Ia) by B a r t ~n . ~ Recently, some of the present authors reported total syntheses of (&)-galanthamine (Ia) and (&)-epigalanthamine (IIa) in good yield from N-(4hydroxyphenethyl) -N-methyl-2-brorr,o-5-hydroxy-4methoxybenzamide (IIIa) via the enone-type compound (IVa) by application of phenolic oxidation.' Since

The configuration of the quaternary ammonium salts (Va and Vb) from 3‐benzyl‐1,2,3,4,5,6‐hexahydro‐8‐hydroxy‐6,11‐dimethyl‐2,6‐methano‐3‐benzazocine. (II) and 3‐methyl‐2‐butenyl bromide was determined spectroscopically. Moreover, configurational studies on 3‐benzyl (VIa and VIb) and 3‐(3‐methyl‐2‐butenyl)benzazocinium bromides (VIIa and VIIb) were also achieved.