Date Thesis Awarded

5-2016

Document Type

Honors Thesis

Degree Name

Bachelors of Science (BS)

Department

Chemistry

Advisor

Jonathan R. Scheerer

Committee Member

Robert J. Hinkle

Committee Member

Lisa M. Landino

Committee Member

Joshua R. Puzey

Abstract

The total synthesis of peramine, a pyrrolopyrazine natural product containing a guanidine functionality, is described. Peramine is an anti-insect defensive alkaloid produced by fungi endophytic to cool season grasses. Peramine is one of four classes of alkaloid produced by these endophytic fungi and production of this compound is widespread across fungal-grass mutualisms. Unique to our synthesis of peramine is an enolate alkylation of a pyrrole-fuse diketopiperazine and an amenable route to derivatives of peramine. Our synthesis is comprised of seven steps and three chromatographic separations, making it as efficient as the previous two syntheses and better with respect to total yield.

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Creative Commons License
This work is licensed under a Creative Commons Attribution 4.0 License.

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