Synthesis of chiral urethane N-alkoxycarbonyl tetramic acids from urethane N-carboxyanhydrides (UNCAs)
作者： Jean-Alain Fehrentz , Elisabeth Bourdel , Jean-Christophe Califano , Olivier Chaloin , Chantal Devin
DOI: 10.1016/S0040-4039(00)76757-8
关键词:
摘要: Abstract The synthesis of chiral N-protected tetramic acid derivatives which are important precursors β-hydroxy γ-amino under mild conditions is described. Reaction urethane-N-carboxyanhydrides (UNCAs) with Meldrum's in the presence a tertiary amine, followed by subsequent cyclisation produced derivatives. This procedure applicable to Boc-, Fmoc- and Z- N-carboxyanhydrides.
elsevier.com
sci-hub.se 参考文章(8)
Steven V. Ley, Stephen C. Smith, Peter R. Woodward, Further reactions of t-butyl 3-oxobutanthioate and t-butyl 4-diethyl-phosphono-3-oxobutanthioate : Carbonyl coupling reactions, amination, use in the preparation of 3-acyltetramic acids and application to the total synthesis of fuligorubin A. Tetrahedron. ,vol. 48, pp. 1145- 1174 ,(1992) , 10.1016/S0040-4020(01)88210-7
Tarek S. Mansour, Colleen A. Evans, Decarboxylative Carbon Acylation of Malonates with Aminoacylimidazolides Mediated by Lewis Acids Synthetic Communications. ,vol. 20, pp. 773- 781 ,(1990) , 10.1080/00397919008052321
William D. Fuller, Michael P. Cohen, Mitra Shabankareh, Robert K. Blair, Murray Goodman, Fred R. Naider, Urethane protected amino acid N-carboxyanhydrides and their use in peptide synthesis Journal of the American Chemical Society. ,vol. 112, pp. 7414- 7416 ,(1990) , 10.1021/JA00176A063
Tsutomu Katsuki, Masaru Yamaguchi, The Stereoselective Synthesis ofthreo-3-Hydroxy-4-amino Acids Bulletin of the Chemical Society of Japan. ,vol. 49, pp. 3287- 3290 ,(1976) , 10.1246/BCSJ.49.3287
HAMAO UMEZAWA, TAKAAKI AOYAGI, HAZIME MORISHIMA, MEIKI MATSUZAKI, MASA HAMADA, TOMIO TAKEUCHI, PEPSTATIN, A NEW PEPSIN INHIBITOR PRODUCED BY AGTINOMYGETES The Journal of Antibiotics. ,vol. 23, pp. 259- 262 ,(1970) , 10.7164/ANTIBIOTICS.23.259
K. Rinehart, J. Gloer, R. Hughes, H. Renis, J. McGovren, E. Swynenberg, D. Stringfellow, S. Kuentzel, L. Li, Didemnins: antiviral and antitumor depsipeptides from a caribbean tunicate Science. ,vol. 212, pp. 933- 935 ,(1981) , 10.1126/SCIENCE.7233187
Nathalie Galeotti, Joel Poncet, Laurent Chiche, Patrick Jouin, Diastereofacial selectivity in reduction of chiral tetramic acids Journal of Organic Chemistry. ,vol. 58, pp. 5370- 5376 ,(1993) , 10.1021/JO00072A018
Ulrich Schmidt, Bernd Riedl, Gerhard Haas, Helmut Griesser, Andrea Vetter, Steffen Weinbrenner, Enantioselective and Diastereoselective Formation ofsyn-3-Hydroxy-4-amino Acids (syn-Statines) via Tetramic Acids Synthesis. ,vol. 1993, pp. 216- 220 ,(1993) , 10.1055/S-1993-25834