Malaria, which is caused by a protozoan parasite of the genus Plasmodium, affects nearly all areas in tropical climates infecting 190 million people worldwide with sub-Saharan Africa accounting for the majority of the fatalities. The flinderoles, which were discovered from the bark of the plant, Flindersa amboinensis, have displayed antimalarial activity against a number of parasite lines including Dd2, which is chloroquine resistant.  This activity combined with a good selectivity index (SI) make flinderoles ideal compounds for synthesis and drug development.  A short, modular synthesis of the molecule is envisioned in which the tricyclic core of the flinderoles are constructed and the indole side chain is appended via cross coupling.  An intramolecular Friedel-Crafts reaction between the C-2 position of indole and an allylic alcohol has been used to construct the core this class of natural products.

Progress toward the flinderole alkaloids

243rd National Meeting (2012)

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