Quinoline Alkaloids. Synthesis of Khaplofoline, Ribalinine, and Flindersine

Abstract

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 5 a 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. © 1992, Walter de Gruyter. All rights reserved.