Chemical Society Seminar: Noah Burns- Lipid Natural Products as Inspiration for Total Synthesis, Materials, and Methods

Abstract:

Evolution has produced a fascinating array of lipid structures that dictate the function of biological membranes, and organisms devote considerable energy to the synthesis and maintenance of such compositions. Our group has been studying some of the most exotic lipids observed to date, representing a radical departure from the canonical hydrocarbons that dominate almost all prokaryotic and eukaryotic membranes. Highly unusual polycyclobutane-containing ladderane phospholipids and macrocyclic tetraether lipids have been identified from anaerobic ammonium-oxidizing bacteria and archaea, respectively. Our work has developed syntheses of each of these classes of noncanonical membrane lipids, and material produced therefrom has begun to inform us on their natural functions. These natural products have also inspired us to pursue new approaches to ladder-type small molecules and materials as well as new methods for the synthesis of cyclobutanes. This includes the discovery of a practical way to produce cyclobutadiene, the so-called “Mona Lisa of organic chemistry.” Similar practicality has been achieved in a photochemical process for engaging simple alkenes in cycloadditions that is tolerant of basic nitrogen atoms. This talk will feature discussions of total synthesis, methodology development, biophysical studies, and polymer materials.

Bio:

Noah was born in Oakland, CA but grew up in south central Maine. He attended Columbia University where he was mentored by Professor James Leighton. He obtained his Ph.D. with Professor Phil Baran at the Scripps Research Institute in La Jolla, CA and was then an NIH postdoctoral fellow with Professor Eric Jacobsen at Harvard University. He joined the chemistry faculty at Stanford University in the fall of 2012 and was promoted to Associate Professor in 2019. His research is rooted in synthetic organic chemistry, but his group looks for unique opportunities to interface with other fields. Noah is a passionate mentor, teacher, and lover of dogs.