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Communication | Regular issue | Vol 6, No. 7, 1977, pp.953-957
Published online, 1st January, 1970
DOI: 10.3987/R-1977-07-0953
Concentration Dependent Photoxidation of 13-Hydroxyberberinium Phenolbetaine and Formation of Stable Epidioxy Compound

Yoshikazu Kondo,* Hideo Inoue, and Jiro Imai

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


Irradiation of an oxygenated solution of 13-hydroxyberberinium phenolbetaine 2 in over 0.1% concentrations gave a stable epidioxy derivative, 8,13a-epidioxy-2,3-methylenedioxy-9,10-dimethoxy-13-oxodibenzo[a,g]quinolizidine 4 in 42% yield. Contrast to it, in a below 0.01% solution photoxidation of 2 gave berberal 5 in 56% yield.
The reactions are interpreted as occurring by initial addition of singlet oxygen to give a peroxide intermediate A which subsequently gave 4 and 5 via the 1,2-dioxetane B depending upon concentrations of A, respectively.