Synthesis and olfactory properties of (−)-(1R,2S)-Georgywood |
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Authors: | Georg Frter Urs Müller Fridtjof Schrder |
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Institution: | Givaudan Schweiz AG, Fragrance Research Chemistry, Überlandstrasse 138, CH 8600 Dübendorf, Switzerland |
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Abstract: | The enantiomers of Georgywood® were synthesized from (E)-2-methyl-6-methylene-nona-2,7-diene and methacrylaldehyde followed by oxidation of the Diels–Alder adduct and classical racemate separation of the acid with optically-active N-methylephedrine. Conversion to the final ketone and olfactory evaluation showed that the (?)-(1R,2S)-enantiomer is more powerful by a factor of >100 than its antipode. The absolute configuration was determined by conformational studies and CD-analysis. |
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