Synthetic study of optically active 3-azabicyclo [3.3. 0] octane-2, 6, 8-tricarboxylic acid

Y Arakawa, M Ohnishi, N Yoshimura…

文献索引：Arakawa, Yasushi; Ohnishi, Masafumi; Yoshimura, Norikazu; Yoshifuji, Shigeyuki Chemical and Pharmaceutical Bulletin, 2003 , vol. 51, # 8 p. 1015 - 1020

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被引用次数: 9

摘要

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 ...