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By chromium trioxide oxidation and subsequent acid hydrolysis triacetyl emodine (3) was transferred to the aldehyde in a two-step synthesis. In a more favourable sequence 3 was reacted to the bromomethyl derivative  4  and this solvolyzed to the citreoroseine derivative 5. A second NBS reaction gave  8  which after acid hydrolysis led to emodine aldehyde  (9).  This five-step process proceeded without chromatographic separation in 27% overall yield.

Synthesen von Emodinaldehyd [1] / Synthesis of Emodine Aldehyde [1]