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Communication | Regular issue | Vol 14, No. 6, 1980, pp.817-825
Published online, 1st January, 1970
DOI: 10.3987/R-1980-06-0817
Synthesis of (±)-Kreysiginone, a Homoaporphine and Homoprotoberberines via N-Oxide Intermediates

Tetsuji Kametani,* Masataka Ihara, Makoto Takemura, and Yoshinari Satoh

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


Reaction of 1,2,3,4-tetrahydro-7-hydroxy-1-(3-hydroxy-4-methoxyphenethyl)-6-methoxy-2-methylisoquinoline N-oxide (2) with ferrous sulfate in methanol gave the 2,9-and 2,11-dihydroxyhomoprotoberberines (5 and 6). The 2,10-dihydroxy derivative (8) was obtained by the reaction of 1,2,3,4-tetrahydro-7-hydroxy-1-(4-hydroxy-3-methoxyphenethyl)-6-methoxy-2-methylisoquinoline N-oxide (4) with ferrous sulfate in hot acetic acid. Reaction of the N-oxides (2 and 4) with cuprous chloride in methanol afforded the phenol oxidative coupling products, the homoaporphine (12) and (±)-kreysiginones (13).