An Alternative Route for the Synthesis of (E)-(+)-5(S)-Methylhept-2-en-4-one (Filbertone)

Abstract

We are reporting an alternative methodology to prepare (+)-Filbertone (1), a natural flavor isolated from hazelnut extracts. Commercially available (-)-2(S)-methylbutan-1-ol (2) was used as starting material and the synthesis was carried out in four steps with an overall yield of 42%. The optical rotation and the enantiomeric purity of the final compound were determined.

Keywords

• pyridinium chlorocromate
• Filbertone
• double bond isomerization