Title

Synthesis of Phidianidines A and B

Presenter Information

Brandon Petersen
Jacob Buchanan

Document Type

Oral Presentation

Location

SURC Ballroom C/D

Start Date

16-5-2013

End Date

16-5-2013

Abstract

Phidianidines A and B are compounds originally isolated from the shell-less sea mollusk, Phidiana militaris, in 2011. Testing of phidianidines A and B revealed significant cytotoxicity against C6 rat glioma cells, 3T3-L1 murine embryonic fibroblasts and HeLa human epithelial cervical cancer cells. The phidianidines are unique because they are the first natural products discovered with a 1,2,4-Oxadiazole ring system. Many other man-made medicinal drugs have a 1,2,4- or 1,3,4-Oxadiazole ring. Therefore, there is the possibility for derivatives of phidianidines to be more potent. Total synthesis of phidianidines A and B has been published, but with low yields and an unstable starting material. It is our intent to provide a more concise synthesis of phidianidines A and B using stable starting materials and improve the overall yield of the synthesis. Our convergent approach will start from 1,5-pentadiamine and 6-bromoindole that will be used to create the two precursors that will be combined near the end of the synthesis. This would make our method a more appealing synthesis route for further study and for effective synthesis in industry.

Poster Number

43

Faculty Mentor(s)

Stephen Chamberland

Additional Mentoring Department

Chemistry

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May 16th, 8:20 AM May 16th, 10:50 AM

Synthesis of Phidianidines A and B

SURC Ballroom C/D

Phidianidines A and B are compounds originally isolated from the shell-less sea mollusk, Phidiana militaris, in 2011. Testing of phidianidines A and B revealed significant cytotoxicity against C6 rat glioma cells, 3T3-L1 murine embryonic fibroblasts and HeLa human epithelial cervical cancer cells. The phidianidines are unique because they are the first natural products discovered with a 1,2,4-Oxadiazole ring system. Many other man-made medicinal drugs have a 1,2,4- or 1,3,4-Oxadiazole ring. Therefore, there is the possibility for derivatives of phidianidines to be more potent. Total synthesis of phidianidines A and B has been published, but with low yields and an unstable starting material. It is our intent to provide a more concise synthesis of phidianidines A and B using stable starting materials and improve the overall yield of the synthesis. Our convergent approach will start from 1,5-pentadiamine and 6-bromoindole that will be used to create the two precursors that will be combined near the end of the synthesis. This would make our method a more appealing synthesis route for further study and for effective synthesis in industry.