Date Thesis Awarded

4-2014

Document Type

Honors Thesis

Degree Name

Bachelors of Science (BS)

Department

Chemistry

Advisor

Elizabeth Harbron

Committee Member

Robert Hinkle

Committee Member

John Swaddle

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.

Kelsey Miller Thesis Availability Agreement.pdf (86 kB)
Thesis Availability Agreement

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