title: A monocyclic neodysiherbaine analog: Synthesis and evaluation.
abstract: Monocyclic analog of neuroexcitatory neodysiherbaine has been designed and stereoselectively synthesized in 0.40% yield over total 24 steps starting from d-ribose, by employing domino aldol-Cannizzaro reaction and stereoselective aldol reaction for construction of two quaternary carbon stereogenic centers at C4 and C6 positions, respectively. The hyperactivity of neodysiherbaine in mice was found to deteriorate in the novel analog, upon intracerebroventricular injection.
authors.affiliation: Yokohama City University, Seto 22-2, Kanazawa-ku, Yokohama 236-0027, Japan.
authors.forename: Koichi
authors.initials: K
authors.lastname: Fukushima
authors.affiliation: Yokohama City University, Seto 22-2, Kanazawa-ku, Yokohama 236-0027, Japan.
authors.forename: Yuichi
authors.initials: Y
authors.lastname: Ishikawa
authors.affiliation: Faculty of Fisheries Sciences, Hokkaido University, Hakodate 041-8611, Japan.
authors.forename: Ryuichi
authors.initials: R
authors.lastname: Sakai
authors.affiliation: Yokohama City University, Seto 22-2, Kanazawa-ku, Yokohama 236-0027, Japan. Electronic address: moikawa@yokohama-cu.ac.jp.
authors.forename: Masato
authors.initials: M
authors.lastname: Oikawa
mesh_terms: D000409:Alanine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D000818:Animals; D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D004305:Dose-Response Relationship, Drug; D004353:Drug Evaluation, Preclinical; D009682:Magnetic Resonance Spectroscopy; D051379:Mice; D013329:Structure-Activity Relationship
chemical_list: D019086:Bridged Bicyclo Compounds, Heterocyclic; C438974:neodysiherbaine A; D000409:Alanine
keywords: Aldol reaction; Dihydroxylation; Domino reaction; Excitatory amino acid; Natural product analog; Neodysiherbaine; Neuroactivity; Stereoselective synthesis