title: Synthetic study of optically active 3-azabicyclo[3.3.0]octane-2,6,8-tricarboxylic acid.
abstract: Synthesis of (1R,2S,5S,6R,8S)-3-azabicyclo[3.3.0]octane-2,6,8-tricarboxylic acid (2) from trans-4-hydroxy-L-proline (5) was attempted. A Diels-Alder reaction of 3,4-dehydroproline derivative 9 and cyclopentadiene afforded a single stereoisomer 11. The Diels-Alder adduct was smoothly converted to the hydrochloride of 2 (24) via RuO(4) oxidation. Although some racemization of the material or product was observed during the synthetic processes, the amino acid 24 proved to be optically pure.
authors.affiliation: Faculty of Pharmaceutical Sciences, Hokuriku University, Kanazawa 920-1181, Japan. ya-arakawa@hokuriku-u.ac.jp
authors.forename: Yasushi
authors.initials: Y
authors.lastname: Arakawa
authors.forename: Masafumi
authors.initials: M
authors.lastname: Ohnishi
authors.forename: Norikazu
authors.initials: N
authors.lastname: Yoshimura
authors.forename: Shigeyuki
authors.initials: S
authors.lastname: Yoshifuji
mesh_terms: D009795:Octanes / Q000138:chemical synthesis*; D009904:Optical Rotation; D014233:Tricarboxylic Acids / Q000138:chemical synthesis*
chemical_list: D009795:Octanes; D014233:Tricarboxylic Acids