Total Synthesis of (+)-nemorensic acid: En Route to (-)-callosine

Publication Year:
2016
Usage 154
Downloads 127
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Repository URL:
https://ir.lib.uwo.ca/etd/3742; https://ir.lib.uwo.ca/cgi/viewcontent.cgi?article=5325&context=etd
Author(s):
Vriesen, Matthew R
Tags:
nemorensic acid; callosine; total synthesis; cyclopropane; annulation; Organic Chemistry
article description
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.