Stereoselective synthesis of (2S,3S)-3-N-benzylaminoprolinol and (7S,8R)-7-N-benzylaminopyrrolizidin-3-one

作者: Nicole Langlois , Marie-Odile Radom

DOI: 10.1016/S0040-4039(97)10749-3

关键词:

摘要: Abstract The highly stereoselective synthesis of (2S,3S)-3-N-benzylaminoprolinol and derivatives involved the conjugate addition N-benzylamine to α,β-unsaturated lactam 2. Wittig-Horner reactions with 1-acetyl-3-N-acetyl-N-benzylaminoprolinal provided a simple access (7S,8R)-7-N-benzylaminopyrrolizidin-3-one.

参考文章(27)
Robert E. Ireland, Longbin Liu, An improved procedure for the preparation of the Dess-Martin periodinane Journal of Organic Chemistry. ,vol. 58, pp. 2899- 2899 ,(1993) , 10.1021/JO00062A040
Khalid Ikhiri, A. Ahond, C. Poupat, P. Potier, J. Pusset, T. Sévenet, Plantes de Nouvelle Calédonie, 109. Absouline, Alcaloïde Pyrrolizidinique Nouveau Isole de Hugonia oreogena et Hugonia penicillanthemum Journal of Natural Products. ,vol. 50, pp. 626- 630 ,(1987) , 10.1021/NP50052A008
Stephen L. Taylor, David Y. Lee, J. C. Martin, Direct, regiospecific 2-lithiation of pyridines and pyridine 1-oxides with in situ electrophilic trapping Journal of Organic Chemistry. ,vol. 48, pp. 4156- 4158 ,(1983) , 10.1021/JO00170A071
Ugo Chiacchio, Franco Casuscelli, Antonino Corsaro, Vito Librando, Antonio Rescifina, Roberto Romeo, Giovanni Romeo, α-Amino acids as chiral educts for stereoselective syntheses of pyrrolidine and pyrrolizidine systems☆ Tetrahedron. ,vol. 51, pp. 5689- 5700 ,(1995) , 10.1016/0040-4020(95)00233-X
André Mann, Sylvie Le Coz, Fr仕屍ic Thareau, Maurizio Taddei, Synthesis of (-)-heliotridane and (-)-isoretronecanol via diastereoselective conjugate addition of organocuprates to an enoate deriving from proline Heterocycles. ,vol. 36, pp. 2073- 2080 ,(1993) , 10.3987/COM-93-6423
Nicole Langlois, Nguyen Van Bac, Nathalie Dahuron, Jean-Marc Delcroix, Abdallah Deyine, Dominique Griffart-Brunet, Angèle Chiaroni, Claude Riche, 1,3-Dipolar cycloadditions of nitrones to α,β-unsaturated γ-lactams derived from (S)-pyroglutaminol Tetrahedron. ,vol. 51, pp. 3571- 3586 ,(1995) , 10.1016/0040-4020(95)00100-M
Daniel L. Flynn, Daniel L. Zabrowski, Daniel P. Becker, Roger Nosal, Clara I. Villamil, Gary W. Gullikson, Chafiq Moummi, Dai C. Yang, SC-53116: the first selective agonist at the newly identified serotonin 5-HT4 receptor subtype. Journal of Medicinal Chemistry. ,vol. 35, pp. 1486- 1489 ,(1992) , 10.1021/JM00086A019