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Communication | Regular issue | Vol 12, No. 7, 1979, pp.893-896
Published online, 1st January, 1970
DOI: 10.3987/R-1979-07-0893
Biomimetic Synthesis of Protoberberine Alkaloids and Aporphine Alkaloids through N-Oxide Intermediates

Tetsuji Kametani* and Masataka Ihara

*Pharmaceutical Institute, Tohoku University, Aobayama, Sendai 980-8578, Japan

Abstract

Reaction of (±)-reticuline N-oxide (3) with cuprous chloride in methanol, followed by treatment with sodium hydrosulphite, gave (±)-corytuberine (8) in excellent yield, while phenol oxidative coupling of (±)-orientaline N-oxide (4) was less effective under the same conditions. Treatment of 3 with ferrous sulphate in methanol afforded (±)-coreximine (5) and (±)-scoulerine (6), but formation of the protoberberine (7) from 4 with this reagent required acidic conditions.