145235-87-6Relevant 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).
2-Chloro-1-methoxymethylindole-3-carboxaldehyde: Introduction of nucleophiles into the indole 2-position and an approach to the unusual TrpHis fragment of moroidin
Comber,Moody
, p. 731 - 733 (2007/10/02)
2-Chloro-1-methoxymethylindole-3-carboxaldehyde (3) is an excellent substrate for a range of nitrogen nucleophiles and gives 2-substituted indoles. Use of a histidine based nucleophile results in the formation of the N-(2-indolyl)imidazole (11), a precursor for the unusually substituted tryptophan residue of the bicyclic octapeptide moroidin.
