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Carbazole-1,4-quinol

The carbazole-1,4-quinol alkaloids are also accessible by the iron-mediated arylamine cyclization (Scheme 14). Electrophilic substitution reaction of the arylamine 24 with the complex salts 6a and 6b affords the iron complexes 25. Protection to the acetates 26 and oxidative cyclization with very active manganese dioxide leads to the carbazoles 27, which are oxidized to the carbazole-... [Pg.125]

Scheme 3 Carbazole-l,4-quinone and carbazole-l,4-quinol alkaloids... Scheme 3 Carbazole-l,4-quinone and carbazole-l,4-quinol alkaloids...
In 1988, Nakamura et al. reported the isolation of carbazomycins G (269) and H (270) from the culture broth of Streptoverticillium ehimense. These alkaloids have a structurally unique carbazole-l,4-quinol framework and were obtained from Nature in racemic form. Carbazomycin G showed moderate antifungal activity against... [Pg.103]

The intramolecular oxidative cyclization of the anilinobenzoquinone 940 with a catalytic amount of palladium(II) acetate in the presence of copper(II) acetate in air afforded the carbazole-l,4-quinone 941 in almost quantitative yield. The regioselective introduction of the heptyl side chain at C-1 of the carbazole-l,4-quinone 941 was achieved by a 1,2-addition of the corresponding Grignard reagent to give the carbazole-l,4-quinol 942 in 55% yield. However, 1,4-addition at C-3 and 1,2-addition at C-4 led to the regioisomeric products 943 and 944 as well. Finally, under acidic reaction conditions, the carbazole-l,4-quinol 942 was smoothly transformed to... [Pg.272]

Carbazomycin G and H have been isolated from Streptoverticillium ehimense [38]. In nature carbazomycin G occurs as a racemic mixture and the same is assumed for carbazomycin H. Garbazomycin G was reported to show antifungal activity. The two compounds share a unique structure, namely the carbazole-l,4-quinol moiety. Starting from the appropriate iron complex salt, iron-mediated arylamine cydization provides a simple route to both alkaloids (Scheme 15.10) [39]. [Pg.483]


See other pages where Carbazole-1,4-quinol is mentioned: [Pg.483]    [Pg.119]    [Pg.142]    [Pg.103]    [Pg.255]    [Pg.256]    [Pg.483]    [Pg.293]   
See also in sourсe #XX -- [ Pg.483 ]




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Carbazole-1,4-quinol alkaloids

Quinol

Quinolate

Quinolates

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