Natural product synthesis via indium catalyzed Friedel-Crafts alkylation
Grzybowski, Paul Lawrence
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Natural products are becoming an increasingly valuable resource in the design and development of new drug candidates. Since 2009 natural products have grossed over $16 billion (U.S. dollars) producing 10 out of the top 20 best-selling drugs on the market. Flinderoles, natural products isolated from the Flindersia plant found in Papua New Guinea, are garnering interest in the synthetic organic community due to their antimalarial properties, especially against chloroquine-resistant strains. Malaria is an infectious disease caused by the parasite Plasmodium falciparum which in 2010 led to 216 million cases worldwide, claiming 655,000 victims. Based on previous research in synthesizing 1H-pyrrolo[1,2-a]indole frameworks via an indium catalyzed intramolecular Friedel-Crafts alkylation, we propose an efficient methodology for the synthesis of Flinderole C using a similar protocol. The compound will be synthesized in seven linear steps from tryptamine derivatives becoming shorter than previously reported synthesis (11 linear steps). If proven successful, this scheme will provide efficient alternatives to synthesizing large heteroaromatic-based natural products, aiding in the search for new drug candidates.