Diastereoselective synthesis of 5-hydroxy-8-methoxy-1-oxaspiro[5,5]undeca-7,10-diene-9-one.
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.
Department of Chemistry, University of Northern British Columbia, 3333 University Way, Prince George, BC V2N 4Z9, Canada. plourde@unbc.ca
Guy L
GL
Plourde
Thomas W
TW
Scully
D001547:Benzaldehydes / Q000737:chemistry*; D008968:Molecular Conformation; D011714:Pyrans / Q000138:chemical synthesis*; D013141:Spiro Compounds / Q000138:chemical synthesis*; D013237:Stereoisomerism; D044366:Transition Temperature
D001547:Benzaldehydes; D011714:Pyrans; D013141:Spiro Compounds; C100058:vanillin