ASYMMETRIC SYNTHESES OF (2R,4S)-4-AMINO-4-CARBOXY-2-METHYLPYRROLIDINEAND (2R,4S)-4-AMINO-2-CARBOXY-2-ETHYL-PYRROLIDINE AS NOVEL 2-ALKYL-SUBSTITUTED (-)-CUCURBITINE ANALOGS

Authors
TANAKA K SUZUKI H SAWANISHI H
Citation
K. Tanaka et al., ASYMMETRIC SYNTHESES OF (2R,4S)-4-AMINO-4-CARBOXY-2-METHYLPYRROLIDINEAND (2R,4S)-4-AMINO-2-CARBOXY-2-ETHYL-PYRROLIDINE AS NOVEL 2-ALKYL-SUBSTITUTED (-)-CUCURBITINE ANALOGS, Heterocycles, 43(1), 1996, pp. 205-219
Citations number
20
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Heterocycles → ACNP
ISSN journal
03855414
Volume
43
Issue
1
Year of publication
1996
Pages
205 - 219
Database
ISI
SICI code
0385-5414(1996)43:1<205:ASO(>2.0.ZU;2-#
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-su bstituted (-)-cucurbitine analogues, have been achieved without distur bing C-2 stereogenic center through a route including a diastereoselec tive Bucherer-Bergs reaction of 2-methyl- and 2-ethenyl-4-oxopyrrolidi nes (10) and (24), easily derived from trans-4-hydroxy-L-proline.