Document Type

Honors Project On-Campus Access Only


Thesis Adviser: Rebecca C. Hoye (Dept. of Chemistry, Macalester College)


The marine sponge alkaloids xestospongins and aruguspongines have well-established biological activities, including the inhibition of inositol trisphosphate receptors and the prevention of inositol trisphosphate mediated intracellular calcium release. These alkaloids are highly valuable in the study of the inositol trisphosphate and calcium signaling pathways in cells because few viable alternative inhibitors exist. However, xestospongin C – the most potent of these alkaloids – is not stable during storage. The goal of this study was to implement a thirteen-step synthesis of a xestospongin C derivative, designed to enhance storage stability and provide a reliable inhibitor for the study of these crucial cellular signaling functions.



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