The Maio laboratory is heavily invested in the design and execution of short, efficient syntheses of both natural and natural product-like compounds of biological interest. Current targets include (1) secondary metabolites with undefined or otherwise ambiguous stereo-assignments, (2) neuro-active compounds that regulate intracellular calcium levels, and (3) cytotoxic natural products of mixed biosynthetic origin, specifically depsipeptides. As an important note, much of our work in the natural products arena exploits enantio- and diastereometic relationships between advanced fragments as a means to access both the natural stereoisomer as well as a stereochemically-diverse set of non-natural analogues for biological evaluation. Relying on clues from nature, concurrent with this work, we are also engaged in the exploration of new chemical methods, for complex molecule synthesis.