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Communication | Special issue | Vol 7, No. 1, 1977, pp.45-50
Published online, 1st January, 1970
DOI: 10.3987/S-1977-01-0045
Oxidative Ring Cleavage of Coralyne Alkaloid

Yoshikazu Kondo,* Hideo Inoue, and Jiro Imai

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

Abstract

Oxygenation of coralyne alkaloid, a nonenzymic model of the oxygenase, has been investigated. A solution of dihydrocoralyne 1 or 13-hydroxycoralynium betaine 2 in the presence of sodium alkoxide was allowed to contact with air under illumination of visible light to give 6,7-dimethoxyisoquinolone-1 3 and the corresponding 3-methyl-3-alkoxy-5,6-dimethoxyphthalide 4 or 5. When the same autoxidation was carried out in the presence of borohydride anion, 3 and 3-methyl-5,6-dimethoxyphthalide 6 were obtained along with 13-hydroxycoralydine. Oxygenation of 2 in the presence of cuprous chloride led to 2’-acetylpapaveraldine 11. On the other hand, irradiation of 2 in chloroform in the presence of Rose Bengal gave a 1 : l mixture of 11 and 2’-carbomethoxypapaveraldine 12. The mechanisms were also discussed.