title: Total syntheses of (-)-fructigenine A and (-)-5-N-acetylardeemin.
abstract: The first total synthesis of (-)-fructigenine A and a novel approach to (-)-5-N-acetylardeemin through a common imine intermediate (+)-3 are described. The key steps include highly enantioselective preparation of (+)-3 via domino olefination/isomerization/Claisen rearrangement (OIC) of 5, reductive cyclization (RC), and regioselective oxidation of (-)-4 and a novel assembly of the pyrazino ring of these alkaloids via Ugi three-component reaction/cyclization of (+)-3 with the corresponding amino acid and isonitrile.
authors.affiliation: Meiji Pharmaceutical University, 2-522-1 Noshio, Kiyose, Tokyo 204-8588, Japan.
authors.forename: Satoshi
authors.initials: S
authors.lastname: Takiguchi
authors.forename: Toshimasa
authors.initials: T
authors.lastname: Iizuka
authors.forename: Yuh-suke
authors.initials: YS
authors.lastname: Kumakura
authors.forename: Kohta
authors.initials: K
authors.lastname: Murasaki
authors.forename: Naoko
authors.initials: N
authors.lastname: Ban
authors.forename: Kazuhiro
authors.initials: K
authors.lastname: Higuchi
authors.forename: Tomomi
authors.initials: T
authors.lastname: Kawasaki
mesh_terms: D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D018360:Crystallography, X-Ray; D003500:Cyclization; D006576:Heterocyclic Compounds, 4 or More Rings / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D010084:Oxidation-Reduction; D011744:Pyrimidinones; D013237:Stereoisomerism
chemical_list: D000470:Alkaloids; D006576:Heterocyclic Compounds, 4 or More Rings; D011744:Pyrimidinones; C549274:fructigenine A; C080891:5-N-acetylardeemin