title: A general and concise enantioselective divergent approach to 13-alkyl-substituted ionones.
abstract: A novel enantioselective divergent route to 13-alkyl derivatives of α- and γ-ionone, important components of perfumes and fragrances, is reported. This relatively short and convenient methodology takes advantage of the use of a common intermediate, easily obtained from highly enantiomerically enriched (S)-α-ionone, which avoids the separate installation of the butenone side chain at C(6) for each analog. Olfactory evaluation of synthesized compounds reconfirmed the influence of the hydrophobic interactions of alkyl substituents at C(5) with olfactory receptors (ORs) in the chemoreception of ionones, and suggested that a synperiplanar orientation of C(13) and the lateral chain is the better geometry fitting OR's cavity.
authors.affiliation: Dipartimento di Chimica, Università di Pavia, Via Taramelli 12, I-27100 Pavia (phone: +39-0382-987322; fax: +39-0382-987323).
authors.forename: Serena
authors.initials: S
authors.lastname: Bugoni
authors.forename: Valentina
authors.initials: V
authors.lastname: Merlini
authors.forename: Alessio
authors.initials: A
authors.lastname: Porta
authors.forename: Giuseppe
authors.initials: G
authors.lastname: Zanoni
authors.forename: Giovanni
authors.initials: G
authors.lastname: Vidari
mesh_terms: D006801:Humans; D057927:Hydrophobic and Hydrophilic Interactions; D008958:Models, Molecular; D015394:Molecular Structure; D045792:Norisoprenoids / Q000737:chemistry* / Q000378:metabolism*; D010476:Perfume / Q000737:chemistry* / Q000378:metabolism; D018035:Receptors, Odorant / Q000378:metabolism*; D013237:Stereoisomerism
chemical_list: D045792:Norisoprenoids; D010476:Perfume; D018035:Receptors, Odorant; C011879:alpha-ionone
keywords: Ionones, 13-alkyl-; Modelling studies; Olfactory evaluations