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

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.

pyridinium chlorocromate; Filbertone; double bond isomerization


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