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

1.2.3.4-Tetrahydro-8-hydroxy-7-methoxy-l-(4-methoxyphenethyl)-2-methylisoquinoline (3).•-A solution of 30 mg of the bromoisoquinoline 9 in 40 ml of ethanol was shaken in a current of hydrogen on 10 mg of Raney nickel at room temperature and atmospheric pressure. After absorption of the calculated amount of hydrogen, the catalyst was filtered off and the filtrate was concentrated in vacuo.The residue was basified with 10% ammonia and extracted with chloroform. The extract was washed with water, dried over Na2S04, and evaporated in vacuo to give 20 mg (83.3%) of A-norhomopetaline (3) as a viscous syrup: mass spectrum m/e 327 (M+); ir (CHCls) 3520 cm-1; uv (EtOH) 279.5 and 284 nm (log e 3.41 and 3.40); nmr r

No abstract

No abstract

Das Aminoisochinolin (I) wird in In Schwefelsäure zu (II) diazotiert und (II) durch Photolyse in O‐Benzylhomosalutaridin (III) verwandelt.