Progress toward the total synthesis of the antimalarial bisindole alkaloid villastonine

ORGN 443

Jun Ma, Chunchun Zhang, Jianming Yu, and James M. Cook. Department of Chemistry, University of Wisconsin-Milwaukee, 3210 N. Cramer Street, Milwaukee, WI 53201
Villalstonine is a bisindole formed from the stereospecific condensation of the monomeric indole alkaloids macroline and pleiocarpamine. It has been ioslated from several Alstonia species and has been shown to exhibit antiplasmodial activity. It is much more potent than the corresponding monomeric units against Plasmodium falciparum malaria. An approach towards the total synthesis of villastonine via a Ni catalyzed coupling reaction will be presented.