12/12/17 - 9:45 AM to 11:00 AM
Department Seminar: Myles Warwick Smith, Ph.D.
"Chemical Explorations Inspired by Complex Alkaloids"
Alkaloid natural products have a storied history, contributing both to the development of modern organic synthesis by laying the foundations for modern heterocyclic chemistry as well as to human health through the provision of many crucial therapeutic agents. This presentation details efforts to further explore their potential within two structurally distinct contexts: the akuammiline family of polycyclic indole alkaloids and the polyaromatic, antitumor discorhabdins. Collectively, these endeavors have yielded concise total or formal syntheses of complex members such as (+)-scholarisine A, (+)-strictamine, and several pyrroloiminoquinone alkaloids. Importantly, these efforts have provided novel methodological and strategic advances in C–H functionalization, asymmetric catalysis, metal-mediated cycloisomerization, and pyrone Diels–Alder chemistry, with the latter findings culminating in a method for the assembly of medicinally relevant heterocyclic building blocks. Finally, the discovery of a challenging cyclobutane C–H functionalization in the non-alkaloid context of the ladderane lipids, as well as our preliminary efforts toward a general polycyclobutane synthesis, will also be highlighted.
Event DetailsLocation: 331 Smith HallHost: Professor Joseph TopczewskiSpeakers:
- Myles Warwick Smith, Ph.D.
- Department of Chemistry
- Stanford University