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

Molecules. 2013 Jan 17;18(1):1174-80. doi: 10.3390/molecules18011174.

Abstract

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.

MeSH terms

  • Benzaldehydes / chemistry*
  • Molecular Conformation
  • Pyrans / chemical synthesis*
  • Spiro Compounds / chemical synthesis*
  • Stereoisomerism
  • Transition Temperature

Substances

  • Benzaldehydes
  • Pyrans
  • Spiro Compounds
  • vanillin