Senior Project Advisor
James Vyvyan
Document Type
Project
Publication Date
Spring 2024
Keywords
organic chemistry, total synthesis, natural product, guaipyridine alkaloid, cancer, hepatocellular carcinoma
Abstract
The first total synthesis of rupestines H and I is reported. The two rupestines were synthesized in twelve steps from 6-methylpyridin-3-ol. The key step is an intramolecular Mizoroki-Heck cyclization, which forms the seven-membered carbocycle characteristic of the guaipyridine alkaloids. The rupestines are diastereomers which can be separated by preparative high performance liquid chromatography. Rupestines H and I, guaipyridine alkaloids isolated from Artemisia rupestris, are structurally similar to cananodine, which has activity against two hepatocellular carcinoma cell lines.
Department
Chemistry
Recommended Citation
Long, Aimee and Vyvyan, James, "Total Synthesis of Rupestines H and I" (2024). WWU Honors College Senior Projects. 791.
https://cedar.wwu.edu/wwu_honors/791
Type
Text
Rights
Copying of this document in whole or in part is allowable only for scholarly purposes. It is understood, however, that any copying or publication of this document for commercial purposes, or for financial gain, shall not be allowed without the author’s written permission.
Language
English
Format
application/pdf