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UBC Theses and Dissertations

Total synthesis of streptonigrone Chan, Bryan Ka Ip


This thesis describes the total synthesis of streptonigrone. The centerpiece of our route to the target molecule is a facile one-pot construction of 3-alkylpyridones developed in our laboratory. The quinoline segment of the target molecule, prepared through a Conrad-Limpach synthesis, was condensed with 2-benzyloxy-3,4-dimethoxybenzaldehyde to afford a chalcone intermediate suitable for our pyridine-forming reaction. The assembly of the central 3-methylpyridone ring of the natural product was then accomplished through the merger of the chalcone with 2-cyanopropanamide. Functionalization of the pyridone was then completed through an anionic sequence.

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