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Diastereoselective synthesis of 5-hydroxy-8-methoxy-1-oxaspiro[5,5]undeca-7,10-diene-9-one.

Molecules (Basel, Switzerland) (2013-01-25)
Guy L Plourde, Thomas W Scully
ZUSAMMENFASSUNG

A short five steps synthesis of the title compound from vanillin is described. The racemic spiroether 7 was obtained in 61% yield and in >99% diastereomeric excess (by 1H-NMR) from the corresponding phenolic derivative 3 by oxidation with lead (IV) acetate.

MATERIALIEN
Produktnummer
Marke
Produktbeschreibung

Sigma-Aldrich
Vanillin, ReagentPlus®, 99%
Supelco
Vanillin Schmelzpunktstandard, Pharmaceutical Secondary Standard; Certified Reference Material
Sigma-Aldrich
Vanillin, natural, ≥97%, FCC, FG
Sigma-Aldrich
Vanillin, ≥97%, FCC, FG
Sigma-Aldrich
Vanillin, tested according to Ph. Eur.
Supelco
Vanillin, Pharmaceutical Secondary Standard; Certified Reference Material
Supelco
Kalibriersubstanz von Mettler Toledo, ME 51143093, Vanillin, traceable to primary standards (LGC)
Vanillin, European Pharmacopoeia (EP) Reference Standard