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The formal total synthesis of murrayaquinone A (1) and the total synthesis of furostifoline (5) were completed by the construction of 4-oxygenated 3-methylcarbazoles 7 based on a new type of electrocyclic reaction through 2-alkenyl-3-allenylindole intermediates 8 derived from the 2-alkenyl-3-propargylindoles 9, starting from 2-chloroindole-3-carbaldehyde (11). The N,O-bisbenzyloxymethyl group of 16c and 22 underwent a Birch reduction followed by treatment with Triton B to produce the known 4-hydroxy-3-methylcarbazole (7a) and 4-hydroxy-3-methylfuro[3,2-a]carbazole (7b) as precursors of murrayaquinone A (1) and furostifoline (5), respectively. The trifluoromethanesulfonyloxy-3-methylfuro[3,2-alcarbazole (24), prepared from 7b, was subjected to reductive cleavage to provide furostifoline (5).

chemical and pharmaceutical bulletin/chemical and pharmaceutical bulletin

Novel Syntheses of Murrayaquinone A and Furostifoline through 4-Oxygenated Carbazoles by Allene-Mediated Electrocyclic Reactions Starting from 2-Chloroindole-3-carbaldehyde.