title: A simple and efficient highly enantioselective synthesis of alpha-ionone and alpha-damascone.
abstract: An efficient highly enantioselective (ee > or =99%) synthesis of alpha-ionone and alpha-damascone is described. Both enantiomers of title compounds were synthesized through two straightforward pathways diverging from enantiopure (R)- or (S)-alpha-cyclogeraniol. These versatile building blocks were obtained by regioselective ZrCl(4)-promoted biomimetic cyclization of (6S)- or (6R)-(Z)-6,7-epoxygeraniol, respectively, followed by deoxygenation of the so formed secondary alcohol. The chiral information was encoded by a highly regioselecive Sharpless asymmetric dihydroxylation of inexpensive geranyl acetate.
authors.affiliation: Dipartimento di Chimica Organica, Università di Pavia, Via Taramelli 10, 27100 Pavia, Italy.
authors.forename: Marcella
authors.initials: M
authors.lastname: Bovolenta
authors.forename: Francesca
authors.initials: F
authors.lastname: Castronovo
authors.forename: Alessandro
authors.initials: A
authors.lastname: Vadalà
authors.forename: Giuseppe
authors.initials: G
authors.lastname: Zanoni
authors.forename: Giovanni
authors.initials: G
authors.lastname: Vidari
mesh_terms: D008968:Molecular Conformation; D045792:Norisoprenoids / Q000138:chemical synthesis*; D013237:Stereoisomerism
chemical_list: D045792:Norisoprenoids; C011879:alpha-ionone