Starting with If (340 mg, 0.8 mmol), 37 mg (29%) of 4c, 4.5 mg of (3%) 2f, and 158 mg of unreacted If were separated. Compound 2f was identical with our previous sample prepared by direct para-ortho' phenolic coupling, see ref 16. Preparation of (±)-Pallidine (4a). tV-Formylnorisosalutaridine (4c) (14 mg, 0.04 mmol) was dissolved in methanol (2 mL) and 18% aqueous hydrogen chloride (0.5 mL). The reaction mixture was kept at 50 °C for 24 h under an argon atmosphere and then the methanol was removed under reduced pressure. The residue was basified with ammonium hydroxide and extracted with dichloromethane. The combined organic layer was dried and evaporated. The crude (±)-norisosalutaridine was purified by preparative TLC (dichloromethane-methanol (100:10, v/v) system with initial ammonia treatment), and N-methylated immediately with 98% formic acid (0.5 mL) and 38% aqueous formaldehyde solution (0.5 mL) (1 h reflux). The reaction mixture was basified with ammonium hydroxide and then extracted with dichloromethane. The organic layer was dried and evaporated.The remaining material was finally purified by preparative TLC (dichloromethane-methanol (150:12, v/v) system with initial ammonia treatment) to supply (±)-pallidine (4a) (2.2 mg, 16%), the spectral data of which correspond to those reported earlier13 for the natural product, which does not separate from an authentic sample on TLC.23 72258-92-5; (±)-lf, 72264-51-8; (±)-2c, 87167-77-9; (±)-2f, 87265-23-4; (±)-3b, 87332-78-3; (±)-3c, 88765-44-0; (±)-4a, 27841-88-9; (±)-4b, 37729-28-5; (±)-4c, 88996-27-4; (±)-norisosaletaridine, 89063-54-7; manganese tris(acetonylacetonate), 14284-89-0; vanadyl bis(acetonylacetonate), 3153-26-2.(23) Special thanks are expressed to Prof. M. Shamma, The Pennsylvania State University, who was kind enough to provide us with a sample of natural pallidine.