Synthetic study of optically active 3-azabicyclo[3.3.0]octane-2,6,8-tricarboxylic acid.
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.
Arakawa
Yasushi
Y
Faculty of Pharmaceutical Sciences, Hokuriku University, Kanazawa 920-1181, Japan. ya-arakawa@hokuriku-u.ac.jp
Ohnishi
Masafumi
M
Yoshimura
Norikazu
N
Yoshifuji
Shigeyuki
S
D009795:Octanes / Q000138:chemical synthesis*; D009904:Optical Rotation; D014233:Tricarboxylic Acids / Q000138:chemical synthesis*
D009795:Octanes; D014233:Tricarboxylic Acids