Application of the Crystalline Sponge Method to Revise the Structure of the Phenalenone Fuliginone

Abstract

The structure of fuliginone was revised from a phenyl substituted phenalenone to a hydroxyl substituted phenalenone as a result of its re‐purification via HPLC with subsequent NMR analysis together with an independent synthesis and analysis of the crystal structure, which was secured via the crystalline sponge method. On‐flow High Performance Liquid Chromatography coupled to Nuclear Magnetic Resonance spectroscopy (HPLC‐NMR) was employed to confirm the presence of the natural product in the plant extract and to monitor for any possible degradation or conversion of the compound.

Keywords

• fuliginone
•  phenylphenalenone
•  synthesis
•  crystalline sponge method
•  HPLC‐NMR