Synthesis of Furanokurzin: A Biologically Active Compound
Mentor 1
Stacey Stoffregen
Location
Union Wisconsin Room
Start Date
24-4-2015 2:30 PM
End Date
24-4-2015 3:45 PM
Description
Furanokurzin is a recently discovered compound that was found to inhibit acetylcholinesterase enzymes in vitro and is the target molecule of this research project. Acetylcholinesterase inhibitors are commonly used for treating people with Alzheimer's disease. For instance, Rivastigmine is an acetylcholinesterase inhibitor that is currently used to treat mild to moderate Alzheimer's. When furanokurzin was first discovered, it was extracted from the dry leaves of Macaranga kurzii, a tropical plant found exclusively in Southern Asia. Only nine milligrams of purified furanokurzin was obtained from the extract. In order to confirm that furanokurzin can be used to treat Alzheimer's or other ailments, ample quantities of the compound must be obtained. The most efficient way to produce furanokurzin would be to synthesize the compound in a laboratory, since furanokurzin only exists in a small concentration(~90ppm) from its natural source. The purpose of this research project is to synthesize ample quantities of furanokurzin in the laboratory so that more testing can be done on the compound. A proposed synthetic scheme was devised for the synthesis of furanokurzin using information from an online database and theory of synthetic chemistry. A four step pathway was eventually resolved and all the steps attempted so far were successful. The first two steps are verified and the third step is currently being researched. The first step was a protection reaction followed by a reduction to produce a substituted benzofuran in the second step. The substituted benzofuran that was produced is a new compound that is uncategorized. Now that it is known that the substituted benzofuran can be synthesized, it can now be Brominated via a benzylic Bromination. It was discovered that the protecting agent in the first step is required for all of the proceeding steps so if the substituted benzofuran can be Brominated in the correct position, a Wittig reaction can be performed on the Brominated benzofuran along with deprotection to ultimately yield Furanokurzin; the target molecule.
Synthesis of Furanokurzin: A Biologically Active Compound
Union Wisconsin Room
Furanokurzin is a recently discovered compound that was found to inhibit acetylcholinesterase enzymes in vitro and is the target molecule of this research project. Acetylcholinesterase inhibitors are commonly used for treating people with Alzheimer's disease. For instance, Rivastigmine is an acetylcholinesterase inhibitor that is currently used to treat mild to moderate Alzheimer's. When furanokurzin was first discovered, it was extracted from the dry leaves of Macaranga kurzii, a tropical plant found exclusively in Southern Asia. Only nine milligrams of purified furanokurzin was obtained from the extract. In order to confirm that furanokurzin can be used to treat Alzheimer's or other ailments, ample quantities of the compound must be obtained. The most efficient way to produce furanokurzin would be to synthesize the compound in a laboratory, since furanokurzin only exists in a small concentration(~90ppm) from its natural source. The purpose of this research project is to synthesize ample quantities of furanokurzin in the laboratory so that more testing can be done on the compound. A proposed synthetic scheme was devised for the synthesis of furanokurzin using information from an online database and theory of synthetic chemistry. A four step pathway was eventually resolved and all the steps attempted so far were successful. The first two steps are verified and the third step is currently being researched. The first step was a protection reaction followed by a reduction to produce a substituted benzofuran in the second step. The substituted benzofuran that was produced is a new compound that is uncategorized. Now that it is known that the substituted benzofuran can be synthesized, it can now be Brominated via a benzylic Bromination. It was discovered that the protecting agent in the first step is required for all of the proceeding steps so if the substituted benzofuran can be Brominated in the correct position, a Wittig reaction can be performed on the Brominated benzofuran along with deprotection to ultimately yield Furanokurzin; the target molecule.
