Studies on the Chemical Constituents of Rutaceous Plants. XXXV. Structural Establishment and Synthesis of Bocconoline. Photochemical Reaction of a Benzo [c] phenanthridinium Salt with Methanol

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The structure of bocconoline, mp 232-233°, which was isolated from Macleaya cordata (WILLD.) R. Br. was established from its spectral data as the formula (1). Bocconoline was photochemically synthesized from chelerythrine (2) and methanol in 59.3% yield using acetone as a sensitizer with a low pressure mercury lamp in nitrogen stream.