NSF Young Investigator: Methodology and Strategy in the Synthesis of Marine Alkaloids and Related Compounds

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9457359 Horne Columbia University New synthetic methodologies and strategies will be developed uner this NSF Young Investigator Award for the construction of structurally complex guanidine-based marine natural products possessing important biological activities. The research will focus on the chemistry of 2-aminoimidazoles, where key targets are saxitoxin and related gonyautoxin alkaloids. A recently discovered 2 + 4 -cycloaddition reaction of 2-aminoimidazoles will be employed to generate tetrahydropurines, which will allow a short synthetic route to saxitoxin and gonyautoxins. This grant from the Organic Dynamics Program supports the research of Professor David A. Horne at Columbia University. Marine naturally occurring compounds that contain basic nitrogen atoms (alkaloids) will be synthesized. Some of the alkaloids to be synthesized are neurotoxins which are found in red-tides. In the course of this research it is anticipated that new synthetic methods will be developed as well as shorter routes to the naturally occurring alkaloids. Related compounds that will be synthesized have potentially interesting medicinal properties.