150355-51-4Relevant academic research and scientific papers
Novel syntheses of murrayaquinone A and furostifoline through 4-oxygenated carbazoles by allene-mediated electrocyclic reactions starting from 2-chloroindole-3-carbaldehyde
Hagiwara,Choshi,Nobuhiro,Fujimoto,Hibino
, p. 881 - 886 (2007/10/03)
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-a]carbazole (24), prepared from 7b, was subjected to reductive cleavage to provide furostifoline (5).
New syntheses of murrayaquinone A and furostifoline
Hagiwara, Hitomi,Choshi, Tominari,Fujimoto, Hiroyuki,Sugino, Eiichi,Hibino, Satoshi
, p. 1948 - 1949 (2007/10/03)
Starting from 2-chloro-3-formylindole, new syntheses of murrayaquinone A and furostifoline were achieved by an allene-mediated electrocyclic reaction involving the indole 2,3-bond.
