Asymmetric synthesis and sensory evaluation of sedanenolide.

Daichi Oguro, Hidenori Watanabe

Index: Biosci. Biotechnol. Biochem. 75(8) , 1502-5, (2011)

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Abstract

The synthesis and sensory evaluation of enantiomeric sets of sedanenolide (1) and 3-butylphthalide (3) are described. The asymmetric synthesis was achieved via the intramolecular Diels-Alder reaction of chiral propargylester (5) which was prepared from optically active propargyl alcohol (4) and 2,4-pentadienoic acid. The sensory evaluation of these enantiomers revealed that there were distinct differences between their aroma character and odor threshold.