title: Asymmetric total synthesis of (-)-leuconoxine via chiral phosphoric acid catalyzed desymmetrization of a prochiral diester.
abstract: The asymmetric total synthesis of (-)-leuconoxine has been achieved. The desymmetrization of a prochiral diester using a chiral phosphoric acid catalyst produced a highly enantioenriched lactam with excellent yield. The ring construction featuring an intramolecular N-acyliminium cyclization and the one-step pyrrolidone formation using Bestmann's ylide was successfully accomplished.
authors.affiliation: Meiji Pharmaceutical University , 2-522-1 Noshio Kiyose, Tokyo 204-8588, Japan.
authors.forename: Kazuhiro
authors.initials: K
authors.lastname: Higuchi
authors.forename: Shin
authors.initials: S
authors.lastname: Suzuki
authors.forename: Reeko
authors.initials: R
authors.lastname: Ueda
authors.forename: Norifumi
authors.initials: N
authors.lastname: Oshima
authors.forename: Emiko
authors.initials: E
authors.lastname: Kobayashi
authors.forename: Masanori
authors.initials: M
authors.lastname: Tayu
authors.forename: Tomomi
authors.initials: T
authors.lastname: Kawasaki
mesh_terms: D029062:Apocynaceae / Q000737:chemistry; D002384:Catalysis; D003500:Cyclization; D026121:Indole Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D007769:Lactams / Q000138:chemical synthesis / Q000737:chemistry; D015394:Molecular Structure; D010756:Phosphoric Acids / Q000737:chemistry*; D011760:Pyrrolidinones / Q000138:chemical synthesis / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D026121:Indole Alkaloids; D007769:Lactams; D010756:Phosphoric Acids; D011760:Pyrrolidinones; C000590191:leuconoxine; C030242:phosphoric acid