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Paper | Special issue | Vol 33, No. 2, 1992, pp.619-630
Published online, 1st January, 1970
DOI: 10.3987/COM-91-S56
Synthesis of 2-Oxa and 2-Aza Analogs of Pyrrolizidine-3,5-diones (Lukes-Sorm Dilactam)

Tatsuo Nagasaka,* Rie Hakamada, Shin-ichi Kunii, and Fumiko Hamaguchi

*Tokyo University of Pharmacy and Life Science, 1432-1 Horinouchi, Hachioji, Tokyo 192-0392, Japan

Abstract

The synthesis of 2-oxa and 2-aza analogs of pyrrolizidine-3,5-dione (Lukes-Sorm dilactam), which has amnesia reversal activity, is reported. Optically active (+)-2-oxa and (+)-2-aza analogs [ (+)-2 and (+) -3 ] and racemic 2-aza analog and its 1-methoxycarbonyl derivatives [(±) -3 and (±)-13 and -14 ] were prepared from (-)-S -pyroglutamic acid and succinimide, respectively.