Carbohydrates are the most abundant organic molecules on earth and are critical to a myriad of biological processes. The Vanderbilt Laboratory for Glycoscience uses a blend of synthetic organic chemistry and microbiology to elucidate the biological roles of carbohydrates, with a foci on advances in chemical synthesis and learning new mechanistic concepts. Emerging areas in the lab focus on the synthesis and evaluation of complex alkaloids. Our discussion will be divided into two categories: application of the host defense properties of human milk and the synthesis of iboga alkaloids.