title: Synthesis of (-)-Vulcanolide by enantioselective protonation.
abstract: 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.
authors.affiliation: Firmenich SA, Corporate R&D Division P.O. Box 239, 1211 Geneva 8, Switzerland. charles.fehr@firmenich.com
authors.forename: Charles
authors.initials: C
authors.lastname: Fehr
authors.forename: Nathalie
authors.initials: N
authors.lastname: Chaptal-Gradoz
authors.forename: José
authors.initials: J
authors.lastname: Galindo
mesh_terms: 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*
chemical_list: D005229:Fatty Acids, Monounsaturated; D013764:Tetrahydronaphthalenes; C473046:vulcanolide; C008563:musk; D001554:Benzene