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Synthesis and Olfactory Evaluation of (+)- and (−)-γ-Ionone

✍ Scribed by Claudio Fuganti; Stefano Serra; Alessandro Zenoni

Publisher
John Wiley and Sons
Year
2000
Tongue
German
Weight
100 KB
Volume
83
Category
Article
ISSN
0018-019X

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✦ Synopsis

The synthesis of enantiomerically pure ()-and (À)-g-ionone 3 is reported. The first step in the synthesis is the diastereoisomeric enrichment of 4-nitrobenzoate derivatives of racemic g-ionol 12. The enantioselective lipase-mediated kinetic acetylation of g-ionol 13b afforded the acetate 14 and the alcohol 15, which are suitable precursors of the desired products (À)-and ()-3, respectively. The olfactory evaluation of the g-ionone isomers shows a great difference between the two enantiomers both in fragrance response and in detection threshold. The selective reduction of (À)-3 and ()-3 to the g-dihydroionones (À)-(R)-16 and ()-(S)-17, respectively, allowed us to assign unambiguously the absolute configuration of the g-ionones.

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