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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.[1]


  1. Synthetic study of optically active 3-azabicyclo[3.3.0]octane-2,6,8-tricarboxylic acid. Arakawa, Y., Ohnishi, M., Yoshimura, N., Yoshifuji, S. Chem. Pharm. Bull. (2003) [Pubmed]
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