Analogues of jasmine lactone and cis-jasmone, bearing cyclopropane rings instead of double bonds, were synthesized and their odour characteristics were examined. Modification of the cyclopentenone ring of cisjasmone reduced both the quality and the intensity of the original odour. Cyclopropanation of the pentenyl side chains did not increase the odour intensity, but it gave a fruity characteristic to the original odours of cis-jasmone and jasmine lactone.
Analogues of methyl jasmonate bearing a cyclopropane ring were synthesized and their odour characteristics were examined. Cyclopropanation of the pentenyl side chains not only increased the odour intensity, but also gave a mossy mushroom characteristic when compared with the original odour. Modification of the cyclopentanone to fix the cis ring geometry reduced both the quality and intensity of the original odour.
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