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Paper | Special issue | Vol 40, No. 1, 1995, pp.293-300
Published online, 1st January, 1970
DOI: 10.3987/COM-94-S30
Dimeric Murrayafoline A, a potential Bis-Carbazole Alkaloid: 'Biomimetic' Synthesis, Atropoisomer Separation, and Antimalarial Activity

Gerhard Bringmann, Alfons Ledermann and Guido François

*Institüte of Organic Chemistry, University of Würzburg, Am Hubland, D-97074 Würzburg, Germany


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 a chiral phase was developed. Both the mono- and the dimeric phenolic carbazoles displayed in vitro antimalarial activity against Plasmodium falciparum.