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Synthesis and Olfactory Evaluation of (+)‐ and (−)‐ γ ‐Ionone
Author(s) -
Fuganti Claudio,
Serra Stefano,
Zei Alessandro
Publication year - 2000
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/1522-2675(20001004)83:10<2761::aid-hlca2761>3.0.co;2-9
Subject(s) - chemistry
The synthesis of enantiomerically pure (+)‐ and (−)‐ γ ‐ionone 3 is reported. The first step in the synthesis is the diastereoisomeric enrichment of 4‐nitrobenzoate derivatives of racemic γ ‐ionol 12 . The enantioselective lipase‐mediated kinetic acetylation of γ ‐ionol 13b afforded the acetate 14 and the alcohol 15 , which are suitable precursors of the desired products (−)‐ and (+)‐ 3 , respectively. The olfactory evaluation of the γ ‐ionone isomers shows a great difference between the two enantiomers both in fragrance response and in detection threshold. The selective reduction of (−)‐ 3 and (+)‐ 3 to the γ ‐dihydroionones (−)‐( R )‐ 16 and (+)‐( S )‐ 17 , respectively, allowed us to assign unambiguously the absolute configuration of the γ ‐ionones.