Date Thesis Awarded
5-2024
Access Type
Honors Thesis -- Access Restricted On-Campus Only
Degree Name
Bachelors of Science (BS)
Department
Chemistry
Advisor
Jonathan Scheerer
Committee Members
Christopher Abelt
Robert Hinkle
Hannes Schniepp
Abstract
Onychine, eupolauridine, and 1-azafluoranthene are three distinct pyridine-containing alkaloids with recognized bioactivities in each of their own respectives. This thesis describes a unified synthetic approach to access all three alkaloids via a shared tricyclic 1,2,4-traizine precursor. The total synthesis of onychine was achieved featuring an inverse electron-demand Diels-Alder/retro-Diels-Alder cycloaddition/cycloreversion, a nucleopholic aromatic substitution reaction, and a silver-catalyzed protodecarboxylation. The progress toward the syntheses of eupolauridine and 1-azafluoranthene will be described.
Recommended Citation
Ma, Yun, "A Unified Synthetic Approach to Onychine, Eupolauridine, and 1-Azafluoranthene via A Shared 1,2,4-Triazine Precursor" (2024). Undergraduate Honors Theses. William & Mary. Paper 2106.
https://scholarworks.wm.edu/honorstheses/2106
