The rich structural diversity, intriguing molecular architectures, and potent biological activities of natural products make these compounds compelling targets for synthesis. However, chemists remain limited by the available methods for the efficient construction of many structural motifs.

1. Synthesis of natural products with conformational chirality.

In molecules that possess sp3-hybridized stereogenic carbon atoms, identification of chirality is trivial.  However, in molecules that do not possess such atoms, the identification of the presence of chirality is not straightforward, especially when attempting to distinguish between achiral and racemic compounds.  Furthermore, demonstrating the existence of molecular chirality using experimental techniques is rare, especially when attempting to distinguish between achiral and racemic molecules.  Our group is interested in the synthesis and study of natural products and related molecules that possess chirality by virtue of their conformation.  We are developing new synthetic methods to access these beautiful molecular architectures.  Examples of “home-grown” reactions and related targets are shown schematically below.

Research 1

 

image 2

 

image 3

  

2. Radical Reactions for Alkaloid Synthesis

Single electron processes (i.e. radical reactions) offer huge potential for the synthesis of alkaloids. Specifically, carbon-centered radicals are generally tolerant of heteroatom lone pairs and acidic O–H and N­–H hydrogens. We are actively developing methods for C–C bond formation involving nitrogen-rich functional groups.  Examples of two such reactions we have created are shown below.  Current efforts are directed at the application of these reactions in the synthesis of various nitrogen-rich alkaloids.

Research 4

 

image 5 

 

3. New Complexity-Building Reactions for Synthesis

Our group is interested in creating new reactions that build complex molecular architectures.  In addition to the novel reactions discussed above, we have created a number of new processes for chemical synthesis.  Specific interests include the Diels–Alder reaction of heteroarenes, cross-coupling reactions, and novel redox processes.  Examples of reactions developed in our lab are shown below.

Research 6

 

image 7