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Paper | Special issue | Vol 47, No. 2, 1998, pp.911-919
Published online, 1st January, 1970
DOI: 10.3987/COM-97-S(N)100
Lead Tetraacetate Oxidation of (±)-N-Acylnoraporphines: Facile Synthesis of 4α-Hydroxynoraporphines and 4α-Hydroxyaporphines

Hiromichi Ogasawara, Masaji Suzuki, Tomohiro Shiohara, and Osamu Hoshino*

*Faculty of Pharmaceutical Sciences, Science University of Tokyo, 12, Ichigaya Funagawara-machi, Shinjuku-ku, Tokyo 162-0826, Japan


Lead tetraacetate oxidation of N-trifluoroacetylwilsonirine (4a) and -nordomesticine (4b) in acetic acid at room temperature gave exclusively 4α-acetoxy-N-trifluoroacetylwilsonirine (7a) and -nordomesticine (7b), which were also obtained in good yield by oxidation in dichloromethane at 0°C and successive treatment with acetic acid. N-Ethoxy-carbonylwilsonirine (6a) was converted into 4α-hydroxyglaucine (epicataline)(15a) by the present methodology.