Issue Date: February 27, 2012
Arthur C. Cope Scholar: Jeffrey Aubé
Jeffrey Aubé, 53, had little exposure to chemistry while growing up.
His mother was a nurse, and his father, a pipe fitter. Aubé dreamed of becoming a musician.
“I wasn’t interested in chemistry when I was young,” Aubé says. “I went to college completely unencumbered by any intention of going into science.”
But at the University of Miami, Aubé excelled in his chemistry courses and began conducting research in the lab of Robert E. Gawley, then a chemistry professor at the university. “All of a sudden, I was experiencing organic chemistry in a completely different way than I had seen it in class,” Aubé says. “I fell in love with research.”
Aubé earned a B.S. degree in chemistry from the University of Miami and a Ph.D. in organic chemistry from Duke University. He went on to complete a postdoc at Yale University. Aubé is the first person in his family to earn a college degree.
Today, Aubé is a professor of medicinal chemistry at the University of Kansas. His research group is best known for its discovery of the intramolecular Schmidt reaction, in which an alkyl azide and a ketone react to form a lactam.
In the classic Schmidt reaction, a six-membered ring such as cyclohexanone can be converted into a seven-membered ring. “If you use our variation, you can attach the azide to the cyclohexanone so your product now has two rings associated with it, and it just so happens that those kinds of two-ring structures with a nitrogen at one of the ring fusions are present in a lot of different natural products,” Aubé says.
The intramolecular Schmidt reaction “allows one to consider synthesis of otherwise untouchable targets, such as the prototypical twisted amide 2-quinuclidone,” says Brian M. Stoltz, professor of chemistry at California Institute of Technology. “In my own research, we were able to construct this long-standing target only through the use of the intramolecular Schmidt reaction.”
Using the intramolecular Schmidt reaction, Aubé says, members of his group have made a number of alkaloids isolated from frog toxins. They’ve also made alkaloids from traditional Chinese medicine, such as the molecule stenine. Aubé’s group was able to reduce the number of steps in its previous synthesis of stenine by more than half.
“What is most impressive about Jeff is that the field learns something it did not know every time he discloses one of his publications,” says Dale L. Boger, professor of chemistry at Scripps Research Institute.
Aubé continues to develop new methodologies and uses those reactions to build chemical libraries. He screens those libraries and follows up on interesting biological leads for potential drugs.
“Jeffrey Aubé has consistently built a record of excellence in the development of synthetic methods and their application to the syntheses of natural products, physical organic chemistry, and bioorganic chemistry,” says Barbara N. Timmermann, professor and chair of the department of medicinal chemistry at the University of Kansas. “All of these efforts are characterized by an unusual degree of creativity, attention to detail, rigor, and above all, individuality.”
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