title: Practical total syntheses of acromelic acids A and B.
abstract: Practical total syntheses of acromelic acids A (1) and B (2), which have potent neuro-excitatory activity, were accomplished in 13 (36% total yield) and 17 steps (6.9% total yield), respectively, from 2,6-dichloropyridine (8). Regioselective transformation of symmetric 8 provided nitroalkenes 15 and 16. The pyrrolidine ring was efficiently constructed by Ni-catalyzed asymmetric conjugate addition followed by intramolecular reductive amination.
authors.affiliation: School of Pharmaceutical Sciences, University of Shizuoka , 52-1 Yada, Suruga-ku, Shizuoka 422-8526, Japan.
authors.forename: Hitoshi
authors.initials: H
authors.lastname: Ouchi
authors.forename: Aya
authors.initials: A
authors.lastname: Asahina
authors.forename: Tomohiro
authors.initials: T
authors.lastname: Asakawa
authors.forename: Makoto
authors.initials: M
authors.lastname: Inai
authors.forename: Yoshitaka
authors.initials: Y
authors.lastname: Hamashima
authors.forename: Toshiyuki
authors.initials: T
authors.lastname: Kan
mesh_terms: D000586:Amination; D002384:Catalysis; D006843:Hydrocarbons, Chlorinated / Q000737:chemistry; D007608:Kainic Acid / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D015394:Molecular Structure; D009498:Neurotoxins / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D019906:Nuclear Magnetic Resonance, Biomolecular; D011725:Pyridines / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: C000588842:2,6-dichloropyridine; D006843:Hydrocarbons, Chlorinated; D009498:Neurotoxins; D011725:Pyridines; C051743:acromelic acid A; D007608:Kainic Acid; C438458:acromelic acid B