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Auwers synthesis

Auwers synthesis

The Auwers synthesis is a series of organic reactions forming a flavonol from a coumarone. This reaction was first reported by Karl von Auwers in 1908.

The Auwers synthesis

The first step in this procedure is an acid catalyzed aldol condensation between benzaldehyde and a 3-cyclooxapentanone to an o-hydroxychalcone. Bromination of the alkene group gives a dibromo-adduct which rearranges to the flavonol by reaction with potassium hydroxide.

Mechanism

A possible mechanism for the rearrangement step is shown below:

Mechanism

References

References

  1. K. Auwers, K. Müller, "Umwandlung von Benzal-cumaranonen in Flavonole", ''[[Ber. Dtsch. Chem. Ges.]]'', '''41''', 4233–4241 (1908) ({{doi. 10.1002/cber.190804103137).
  2. K. v. Auwers, P. Pohl, "Über die Umwandlung von Benzalcumaranonen in Flavonole", ''[[Liebigs Ann. Chem.]]'', '''405''', 243–294 (1914) ({{doi. 10.1002/jlac.19144050302).
  3. K. v. Auwers, P. Pohl, "Eine Synthese des Fisetins", ''[[Ber. Dtsch. Chem. Ges.]]'', '''48''', 85–90 (1915) ({{doi. 10.1002/cber.19150480114).
  4. K. v. Auwers, "Zur Bildung von Flavonolen aus Benzal-cumaranonen", ''[[Ber. Dtsch. Chem. Ges.]]'', '''49''', 809–819 (1916) ({{doi. 10.1002/cber.19160490188).
  5. K. v. Auwers, E. Auffenberg, "Über Cumaranone und Hydrindone", ''[[Ber. Dtsch. Chem. Ges.]]'', '''52''', 92-113 (1919) ({{doi. 10.1002/cber.19190520114).
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