M. Christina White
Department of Chemistry
University of Illinois
270 Roger Adams Laboratory
600 South Mathews Ave.
Urbana, IL 61801
Among the frontier
challenges in chemistry in the 21st century are (1) increasing control
of chemical reactivity and (2) synthesizing complex molecules with higher
levels of efficiency. Although it has been well demonstrated that given
ample time and resources, highly complex molecules can be synthesized
in the laboratory, too often current methods do not allow chemists to
match the efficiency achieved in Nature. This is particularly relevant
for molecules with non-polypropionate-like oxidation patterns (e.g.
Taxol). Traditional organic methods for installing oxidized functionality
rely heavily on acid-base reactions that require extensive functional
group manipulations (FGMs) including wasteful protection-deprotection
sequences. Due to their ubiquity in complex molecules and inertness
to most organic transformation, C-H bonds have typically been ignored
in the context of methods development for total synthesis. My laboratory
has initiated a program to develop highly selective oxidation methods,
similar to those found in Nature, for the direct installation of oxygen,
nitrogen and carbon functionalities into allylic and aliphatic C-H
bonds of complex molecules and their intermediates. Unlike Nature which
uses elaborate enzyme active sites, we rely on the subtle electronic
and steric interactions between C-H bonds and small molecule transition
metal complexes to achieve high selectivities. Gaining a fundamental
and predictive understanding of these interactions through mechanistic
studies is one of the main goals and discovery engines of our research.
Using these methods, my group aims to develop novel strategies for streamlining
the process of complex molecule synthesis. Collectively, we aim to change
the way that complex molecules are constructed by redefining the reactivity
principles of C-H bonds in complex molecule settings.