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

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.

Keywords

• synthesis
• diastereoselective
• spirolactone
• spiroether
• spirocompound
• dienone
• oxidation
• lead tetraacetate