Title

Concise total synthesis of phidianidine A and B

Presenter Information

Jacob Buchanan

Document Type

Oral Presentation

Location

SURC Ballroom C/D

Start Date

15-5-2014

End Date

15-5-2014

Keywords

Medicinal Chemistry, Organic Chemistry, Total Synthesis

Abstract

Phidianidine A and B aroused our interest because they were the first chemicals found in nature that contain a cyclic arrangement of one oxygen atom, two nitrogen atoms, and two carbon atoms called an oxadiazole. Several medicinal chemicals made by humans also contain this cyclic motif. In addition, because phidianidine A and B kill cervical, brain, and spinal cancer cells, we and others have sought to prepare these chemicals in the laboratory and develop them into new chemotherapy drugs. Yield for the key step in each known laboratory preparation of phidianidine A and B varies widely (from 15 to 75 percent). Our four-step laboratory preparation of phidianidine A and B is the shortest preparation to date, and we hope to increase our yield of the key step. Optimizing the key step would not only bolster the utility of our phidianidine preparation, but would expand the efficiency of this transformation to prepare other medicinal compounds.

For this presentation, Jacob Buchanan received a College of the Sciences Best Poster Presentation Award for 2014.

Poster Number

15

Faculty Mentor(s)

Chamberland, Stephen

Additional Mentoring Department

Chemistry

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May 15th, 8:30 AM May 15th, 11:00 AM

Concise total synthesis of phidianidine A and B

SURC Ballroom C/D

Phidianidine A and B aroused our interest because they were the first chemicals found in nature that contain a cyclic arrangement of one oxygen atom, two nitrogen atoms, and two carbon atoms called an oxadiazole. Several medicinal chemicals made by humans also contain this cyclic motif. In addition, because phidianidine A and B kill cervical, brain, and spinal cancer cells, we and others have sought to prepare these chemicals in the laboratory and develop them into new chemotherapy drugs. Yield for the key step in each known laboratory preparation of phidianidine A and B varies widely (from 15 to 75 percent). Our four-step laboratory preparation of phidianidine A and B is the shortest preparation to date, and we hope to increase our yield of the key step. Optimizing the key step would not only bolster the utility of our phidianidine preparation, but would expand the efficiency of this transformation to prepare other medicinal compounds.

For this presentation, Jacob Buchanan received a College of the Sciences Best Poster Presentation Award for 2014.