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Paper | Regular issue | Vol 43, No. 1, 1996, pp.205-219
Published online, 1st January, 1970
DOI: 10.3987/COM-95-7277
Asymmetric Syntheses of (2R, 4S)-4-Amino-4-carboxy-2-methylpyrrolidine and (2R, 4S)-4-Amino-2-carboxy-2-ethylpyrrolidine as Novel 2-Alkyl-substituted (-)-Cucurbitine Analogues

Ken-ichi Tanaka*, Hirokazu Suzuki, and Hiroyuki Sawanishi

*Faculty of Pharmaceutical Science, Hokuriku University, Ho-3, Kanagawa-machi, Kanazawa 920-11, Japan

Abstract

Asymmetric syntheses of (2R,4S)-4-amino-4-carboxy-2-methylpyrrolidine (1) and (2R,4S)-4-amino-4-carboxy-2-ethylpyrrolidine (2) as 2-alkyl-substituted (-)-cucurbitine analogues, have been achieved without disturbing C2 stereogenic center through a route including a diastereoselective Bucherer-Bergs reaction of 2-methyl- and 2-ethenyl-4-oxopyrrolidines (10) and (24), easily derived from trans-4-hydroxy-L-proline.