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Reaction of 4-hydroxy-3-prenylquinolin-2(1 H)one (5 a) with iodine and silver acetate gave a iodopyranoquinoline (6 a), which was then converted into the alkaloids khaplofoline (1) and ribalinine (2). Reaction of 5a with iodine and mercuric oxide afforded a mixture of 6a and its angular isomer 7 a; the coversion of latter into flindersine (10) is described.

Quinoline Alkaloids. Synthesis of Khaplofoline, Ribalinine, and Flindersine