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Total Synthesis of Peramine, a Defensive Alkaloid Produced by Endophytic Fungi of Cool Season Grasses Possessing Anti-Insect Properties

Nelli, Matthew Rolfe
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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2016-05-01
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Undergraduate Honors Theses
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Nelli_Honors_Thesis_Final_Draft.pdf
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Scheerer, Jonathan R.
Hinkle, Robert J.
Landino, Lisa M.
Puzey, Joshua R.
Department
Chemistry
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https://scholarworks.wm.edu/handle/internal/12719
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