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A Unified Synthetic Approach to Onychine, Eupolauridine, and 1-Azafluoranthene via A Shared 1,2,4-Triazine Precursor

Ma, Yun
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.
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2024-05-01
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Undergraduate Honors Theses
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A_Unified_Synthetic_Approach_to_Onychine__Eupolauridine__and_1_Azafluoranthene_via_A_Shared_1_2_4_Triazine_Precursor.pdf
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Scheerer, Jonathan
Abelt, Christopher
Hinkle, Robert
Schniepp, Hannes
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Chemistry
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https://scholarworks.wm.edu/handle/internal/11583
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