Research Interests: Nature provides us with a tremendous variety of small molecules that possess fascinating structure and potent medicinal properties. Their biological origin is as diverse as their chemical composition (see below). The need to confirm the molecular structure of these entities, as well as prepare sizeable quantities for biological evaluation and clinical use, drives organic chemists towards their total synthesis.  Heterocycles, meaning rings with at least one atom that is not carbon, serve as the platform for innumerable compounds of medicinal interest. Research in this group aims to synthesize naturally occurring heterocycles with significant biological function (anticancer, antimalarial, neuromodulatory).  We also are in the process of isolating and identifying natural products from local sources.

To concurrently advance the scope of organic synthesis, novel ring formation strategies are being explored in our research group. The strategies center around the fragmentation of substituted cyclopropanols, strained compounds which can be ruptured in a highly controlled fashion.  One such reaction recently developed in our group for the formation of oxepanes (7-membered rings with one oxygen atom), along with its mechanism, is shown below.  

Publication of this development has appeared in Organic Letters.  (PDF)

 

Natural Product Isolation Project:  Globally, amphibians face one of the largest extinction rates in the animal kingdom. Although habitat destruction is a major cause of amphibian extinctions, infection from the fungal pathogen, Batrachochytrium dendrobatidis, is a large contributor.  Our group is working in collaboration with Dr. Reid Harris in the JMU Department of Biology to examine natural products endemic to the skins of local salamanders that may confer protection against this chytrid fungus.  One species we are currently investigating is the Panamanian Golden Frog (right).  The Harris/Minbiole research was presented on  "The Vanishing Frog" on Animal Planet on November 20, 2008, and an interview with KPCM and Dr. Harris aired on With Good Reason, a National Public Radio program for the Virginia and DC region, during the week of September 19, 2009.

Panamanian Golden Frog, photo by B. Gratwicke

         
                Three compounds we've isolated from local salamander sources