220467-41-4

Upstream product

• 220467-40-3 N-(benzyloxymethyl)-3-[1-(benzyloxymethyloxy)prop-2-yn-1-yl]-2-(3-furyl)indole 
• 5059-30-3 2-chloroindole-3-carboxaldehyde 
• 3587-60-8 Benzyloxymethyl chloride 
• 220467-39-0 N-(benzyloxymethyl)-2-(3-furyl)-3-(1-hydroxyprop-2-yn-1-yl)indole 
• 220467-38-9 N-(benzyloxymethyl)-2-(3-furyl)indole-3-carbaldehyde 
• 220467-37-8 2-(3-furyl)indole-3-carbaldehyde 

Relevant 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

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

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.