Anyone who has taken organic chemistry can attest to the fact that synthesis problems are perhaps one of the most challenging aspects of the course. Indeed, much of organic chemistry involves deciding which reactions to carry out on a starting material in order to yield a specific product. Kurtis Magee '08 (Corvallis, Ore.) is spending his summer solving a complicated, real world synthesis problem under the advisement of Ian Rosenstein, associate professor of chemistry. His goal is to carry out a radical reaction to form a vinyl cyclopentane and incorporate it into a bicyclic ring system. The starting material and desired product are shown below.
Overall Reaction Scheme
Magee's reaction is based upon the reaction steps in the well-understood synthesis of vinyl cylcopentanes through the radical reaction of vinyl cyclopropanes with alkenes. His project will test the outcome of this same reaction when done with a vinyl cyclopropane that is incorporated into a larger molecule. Generally speaking, he plans on adding a three-member ring to the double bond of the starting material, opening up the attached ring, and closing the ring so that it forms a new five-member ring.
The product has four chiral centers (i.e. the central atom is attached to four different atoms) and, when he synthesizes it, Magee will work to try to control the attachment of substitutents to these centers.
Hopefully his project will allow for the future synthesis of compounds involving more complex multicyclic ring systems. The radical reaction he is employing could also be applicable to drug design and the synthesis of other interesting natural products and their analogs.
This is Magee's first summer of research at Hamilton, and so far he has found it to be a rewarding experience. He has especially enjoyed the unique intellectual challenges his organic chemistry project has presented. Much of synthesis work involves reading the relevant literature to see what other scientists have done and then seeing how he can apply those methods to his own reaction. Many times, there is more than one right answer to a particular problem, so it is up to the researcher to use his or her own knowledge to find the best solution. Magee says he likes being able to use everything he has learned in class to help develop a plan for how to carry out his reaction. Of course, if he is ever stuck or needs advice on what to do next, he is always able to talk with Rosenstein.
Magee is a chemistry major and comparative literature minor. For his senior thesis, he plans on continuing his current project. Summer research has been especially helpful in this regard because the additional 10 weeks of research over the summer will give him a head start on and a more in-depth examination of his thesis experiment. Hamilton's summer research program has also provided him with the lab experience he needs to prepare for the rigors of graduate school and a future career in the biomedical sciences. When not in the Science Center, Magee is actively involved in many campus organizations. He is a member of the football team and the Hamilton College EMTs (Emergency Medical Technicians) as well as treasurer of the Hamilton College Chemical Society.
-- by Nick Berry '09
Overall Reaction Scheme
Magee's reaction is based upon the reaction steps in the well-understood synthesis of vinyl cylcopentanes through the radical reaction of vinyl cyclopropanes with alkenes. His project will test the outcome of this same reaction when done with a vinyl cyclopropane that is incorporated into a larger molecule. Generally speaking, he plans on adding a three-member ring to the double bond of the starting material, opening up the attached ring, and closing the ring so that it forms a new five-member ring.
The product has four chiral centers (i.e. the central atom is attached to four different atoms) and, when he synthesizes it, Magee will work to try to control the attachment of substitutents to these centers.
Hopefully his project will allow for the future synthesis of compounds involving more complex multicyclic ring systems. The radical reaction he is employing could also be applicable to drug design and the synthesis of other interesting natural products and their analogs.
This is Magee's first summer of research at Hamilton, and so far he has found it to be a rewarding experience. He has especially enjoyed the unique intellectual challenges his organic chemistry project has presented. Much of synthesis work involves reading the relevant literature to see what other scientists have done and then seeing how he can apply those methods to his own reaction. Many times, there is more than one right answer to a particular problem, so it is up to the researcher to use his or her own knowledge to find the best solution. Magee says he likes being able to use everything he has learned in class to help develop a plan for how to carry out his reaction. Of course, if he is ever stuck or needs advice on what to do next, he is always able to talk with Rosenstein.
Magee is a chemistry major and comparative literature minor. For his senior thesis, he plans on continuing his current project. Summer research has been especially helpful in this regard because the additional 10 weeks of research over the summer will give him a head start on and a more in-depth examination of his thesis experiment. Hamilton's summer research program has also provided him with the lab experience he needs to prepare for the rigors of graduate school and a future career in the biomedical sciences. When not in the Science Center, Magee is actively involved in many campus organizations. He is a member of the football team and the Hamilton College EMTs (Emergency Medical Technicians) as well as treasurer of the Hamilton College Chemical Society.
-- by Nick Berry '09
