Scott Sieburth, PhD, Temple University

"Title: Mechanistic and Molecular Complexity in the Pursuit of Synthetic Methods"

Abstract: Our effort to develop efficient methods for complex molecule synthesis, with an emphasis on the invention of novel disconnections, will be described in the context of two studies. Photocycloaddition of 2-pyridones often follow a [4+4] pathway, leading to polycyclic eight-membered ring products. When the pyridone cycloaddition partner is an enyne, the bent, cyclic, highly strained allene photoproduct can undergo several reaction pathways. In the case shown, the efficiently formed cyclooctadienone product can undergo a second photoreaction, a di-π-methane rearrangement. The Kulinkovich-de Meijere reaction between an alkene and an amide forms aminocyclopropanes through two carbon-carbon bond forming reactions. With an appropriate nitrogen substitution, the intermediate can be intercepted, yielding ketones instead. Efforts to understand and control of these transformations will be discussed.