title: Total synthesis of (-)-20-epiuleine via stereocontrolled one-pot asymmetric azaelectrocyclization followed by novel 1,4-addition reaction.
abstract: The first asymmetric total synthesis of an indole alkaloid, (-)-20-epiuleine, containing the 2,3,4-trisubstituted piperidine core, was achieved using a stereocontrolled one-pot asymmetric 6π-azaelectrocyclization followed by a stereoselective 1,4-addition reaction of the unsaturated ester with a Grignard reagent resulting from the novel neighboring participation of the hydroxyl group in cis-aminoindanol as a chiral nitrogen source.
authors.affiliation: School of Science and Technology, Kwansei Gakuin University, Gakuen 2-1, Sanda, Hyogo 669-1337, Japan.
authors.forename: Taku
authors.initials: T
authors.lastname: Sakaguchi
authors.forename: Shohei
authors.initials: S
authors.lastname: Kobayashi
authors.forename: Shigeo
authors.initials: S
authors.lastname: Katsumura
mesh_terms: D000478:Alkylation; D001372:Aza Compounds / Q000737:chemistry*; D003500:Cyclization; D004583:Electrons; D026121:Indole Alkaloids / Q000138:chemical synthesis*; D007659:Ketones / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: C466484:20-epiuleine; D001372:Aza Compounds; D026121:Indole Alkaloids; D007659:Ketones