OSU undergraduate solves long-standing problem in organic chemistry

Sam Bartlett's findings make chemical synthesis faster, more efficient

When Sam Bartlett, an Oregon State University senior in chemistry, put on his lab coat, goggles and latex gloves in the summer of 2010, he didn’t expect to wind up helping organic chemists around the world.

OSU undergraduate Sam Bartlett, right, used basic tools of organic chemistry — from a reflux condenser to nuclear magnetic resonance — to develop a new synthetic chemistry method. He works with Assistant Professor Chris Beaudry in the new Linus Pauling Science Center. (Photo: Karl Maasdam)

OSU undergraduate Sam Bartlett, right, used the tools of organic chemistry — reflux condenser, thin-layer chromotography, nuclear magnetic resonance — to develop a new synthetic chemistry method. He works with Assistant Professor Chris Beaudry in the new Linus Pauling Science Center. (Photo: Karl Maasdam)

With guidance from Chris Beaudry, assistant professor of chemistry, he developed the most efficient and productive method yet reported for a fundamental step commonly used to synthesize new molecules.

Bartlett and Beaudry published their findings in October in the Journal of Organic Chemistry. The research has already drawn the attention of pharmaceutical scientists and has potential in fields from nanotechnology to biochemistry.

“If you’re a synthetic chemist and you want to build complicated molecular architectures – a pharmaceutical, a new material for nanotechnology, a new probe for a biological system – you need to make new chemical bonds,” Beaudry said. “This oxidation is convenient to do, very mild, operationally simple and high yielding. It is the solution to this problem.”

Bartlett’s discovery started with a chance meeting. The student from Corvallis, Oregon, was taking an advanced chemistry course from Beaudry and happened to meet the professor in the Interzone, an off-campus coffee shop. “I asked him if he had any research opportunities in his lab,” Bartlett said.

“I suggested that Sam look into this problem,” Beaudry recalled. “There was some indication that we had a lead hit on how to solve it. Sam took it and ran with it.”

The problem was to convert one commonly used compound (beta-hydroxyketone) to another (beta-diketone). Both are fundamental starting points in the synthesis of more complex organic molecules. Previous methods produced unwanted byproducts and only 30 to 35 percent of the desirable molecule, says Beaudry.

Bartlett found that an oxidant called IBX (o-iodoxybenzoic acid) converts nearly 100 percent of the beta-hydroxyketone to the beta-diketone, thus saving chemists time – and simplifying the synthesis process.

Bartlett, who graduated from Crescent Valley High School, is applying for graduate school, where he intends to focus on synthetic organic chemistry.

“I just like the search for new knowledge,” said Bartlett. “There’s a lot we still don’t know. There are problems out there we still need to solve. Even if I don’t find a solution, I’m contributing to the scientific community.”

Bartlett had support for his research from two programs: the Undergraduate Research, Innovation, Scholarship & Creativity program sponsored by the OSU Research Office, and a Howard Hughes Medical Institute fellowship. He is continuing to work in Beaudry’s lab in the new Linus Pauling Science Center on steps to make a natural plant compound that has potential anti-fungal and anti-inflammatory properties.

Leave a Reply


+ seven = 9