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Synthesis and olfactory properties of (−)-(1R,2S)-Georgywood

Authors
Publisher
Elsevier Ltd
Publication Date
Volume
15
Issue
24
Identifiers
DOI: 10.1016/j.tetasy.2004.11.003

Abstract

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 (−)-(1 R,2 S)-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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