Synthesis of (-)-Vulcanolide by enantioselective protonation.
Two efficient enantioselective syntheses of the more active (S,S)-enantiomer of the powerful musk odorant Vulcanolide are described. In both syntheses, the key step is an enantioselective protonation of a ketone enolate. A third enantioselective protonation, of a thiol ester enolate, was applied for the determination of the absolute configuration of Vulcanolide by comparison with a known compound.
Fehr
Charles
C
Firmenich SA, Corporate R&D Division P.O. Box 239, 1211 Geneva 8, Switzerland. charles.fehr@firmenich.com
Chaptal-Gradoz
Nathalie
N
Galindo
José
J
D001554:Benzene / Q000737:chemistry; D005229:Fatty Acids, Monounsaturated / Q000138:chemical synthesis* / Q000737:chemistry; D009812:Odorants; D013237:Stereoisomerism; D013329:Structure-Activity Relationship; D013764:Tetrahydronaphthalenes / Q000138:chemical synthesis*
D005229:Fatty Acids, Monounsaturated; D013764:Tetrahydronaphthalenes; C473046:vulcanolide; C008563:musk; D001554:Benzene