Studies Directed toward the Synthesis of Asymmetric Loline Alkaloids

Author

Kelsey E. Miller, College of William and MaryFollow

Date Thesis Awarded

4-2014

Access Type

Honors Thesis -- Access Restricted On-Campus Only

Degree Name

Bachelors of Science (BS)

Department

Chemistry

Advisor

Elizabeth Harbron

Committee Members

Robert Hinkle

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 2^nd generation synthesis takes precedent from the 1^st 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 3^rd generation conditions. Other key reactions include Petasis borono-Mannich addition and ring closing metathesis using Hoveyda-Grubbs 2^nd generation catalyst.

Recommended Citation

Miller, Kelsey E., "Studies Directed toward the Synthesis of Asymmetric Loline Alkaloids" (2014). Undergraduate Honors Theses. William & Mary. Paper 36.
https://scholarworks.wm.edu/honorstheses/36

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