Heterocycles p. 293 - 300 (1995)
Update date:2022-08-16
Topics:
Bringmann, Gerhard
Ledermann, Alfons
Francois, Guido
The first total synthesis of a (potential) dimeric carbazole alkaloid is described.After an improved preparation of the monomeric building block, 'biomimetic dimerization' by oxidative phenolic coupling was best achieved with di-tert-butyl peroxide in chlorobenzene, leading to a highly selective formation of the 2,2'-coupled 'dimer', the parent framework of several naturally occurring dimeric carbazole alkaloids.For the atropoenantiomer analysis, a chromatographic procedure on chiral phase was developed.Both the mono- and the dimeric phenolic carbazoles displayed in vitro antimalarial activity against Plasmodium falciparum.
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