title: Stereocontrolled total synthesis of (-)-ephedradine A (orantine).
abstract: The stereocontrolled total synthesis of (-)-ephedradine A has been accomplished. The synthesis features an asymmetric C-H insertion reaction, an intramolecular ester-amide exchange reaction, and a Sharpless asymmetric aminohydroxylation reaction. Construction of the complex macrocyclic ring was performed by Ns-strategy and an intramolecular aza-Wittig reaction.
authors.affiliation: Graduate School of Pharmaceutical Sciences, University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033, Japan.
authors.forename: Wataru
authors.initials: W
authors.lastname: Kurosawa
authors.forename: Toshiyuki
authors.initials: T
authors.lastname: Kan
authors.forename: Tohru
authors.initials: T
authors.lastname: Fukuyama
mesh_terms: D000470:Alkaloids / Q000138:chemical synthesis*; D011073:Polyamines / Q000138:chemical synthesis; D013237:Stereoisomerism
chemical_list: D000470:Alkaloids; D011073:Polyamines; C067643:orantine