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Studies Directed toward the Synthesis of Asymmetric Loline Alkaloids

Miller, Kelsey E
Abstract
This thesis discusses the progress toward the synthesis of asymmetric loline alkaloids. Lolines are polycyclic pyrrolizidine alkaloids that contain four contiguous stereocenters and a strained ether bridge. Lolines are present in symbiotic relationships between grass species and fungal endophytes and act as a natural pesticide and feeding deterrent that protects the grass host from insects, yet are believed to possess low toxicity to mammals. Our Scheerer 2nd generation synthesis takes precedent from the 1st generation Scheerer synthesis, but with some key changes. The synthetic route has fewer steps, a different nitrogen protecting group, and usage of stereoselective tethered aminhydroxylation 3rd generation conditions. Other key reactions include Petasis borono-Mannich addition and ring closing metathesis using Hoveyda-Grubbs 2nd generation catalyst.
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2014-04-01
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Undergraduate Honors Theses
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Kelsey_Miller_Honors_Thesis_Loline_Alkaloids.pdf
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Advisor
Harbron, Elizabeth
Hinkle, Robert
Swaddle, John
Department
Chemistry
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https://scholarworks.wm.edu/handle/internal/12059
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