Synthesis and odor description of optically active cyclopropanated analogues of geraniol, nerol, nor-leaf alcohol, and matsutake alcohol

Both enantiomers of cyclopropanated analogues of geraniol, nerol, nor-leaf alcohol, and matsutake alcohol were synthesized and their odor properties evaluated. Odor characters in enantiomeric pairs were similar in the geraniol series. The (+)-(2R,3S)-nerol derivative showed various odor aspects. From the results of nor-leaf alcohol derivatives, an interaction between the (2-re,3-re)-face of nor-leaf alcohol and the human olfactory receptor was suggested. The odor of (3R)-matsutake alcohol derivative was superior to the enantiomer.

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(−)-(2S,3R)-2,3-Methano-3,7-dimethyl-6-octen-1-olC11H20OEe = >95%[α]D25 = −8.3 (c 1.0, Et2O)Source of chirality: enantioselective cyclopropanationAbsolute configuration: (2S,3R)

(−)-(R)-1,2-Methano-3-octanolC9H18OEe = 99.2%[α]D25 = −0.3 (c 0.65, Et2O)Source of chirality: (R)-1-octen-3-olAbsolute configuration: (R)