Degree
Master of Science
Program
Chemistry
Supervisor
Dr Michael Kerr
Abstract
An intramolecular oxime ether cyclopropane annulation developed in 2008 by Kerr has been shown to form 2,5-trans and 2,5-cis pyrrolidines in a stereodivergent fashion. When the oxime ether is functionalized with an enantioenhanced α-hydroxy substitutent and a leaving group, the pyrrolizidine core of (-)-callosine can be accessed in short order. Callosine is a structurally unique pyrrolizidine alkaloid isolated from Mexican flowering plant Senecio callosus. In an effort to complete the total synthesis, the total synthesis of (+)-nemorensic acid, the necic acid component of the callosine, has been established. Attempts at appending the ansa bridge via esterification and macrolactonization are discussed.
Recommended Citation
Vriesen, Matthew R., "Total Synthesis of (+)-nemorensic acid: En Route to (-)-callosine" (2016). Electronic Thesis and Dissertation Repository. 3742.
https://ir.lib.uwo.ca/etd/3742