Synthesis of novel N-cyclopentenyl-lactams using the Aubé reaction.
作者： Madhuri V Shinde , Rohini S Ople , Ekta Sangtani , Rajesh Gonnade , D Srinivasa Reddy
DOI: 10.3762/BJOC.11.119
关键词:
摘要: A novel and convenient method utilizing the Aube reaction to access a new class of compounds that are similar carbocyclic nucleosides is reported. The azido alcohol derived from Vince lactam undergoes with various cyclic ketones give cyclopentenyl-substituted lactams. Upon dihydroxylation, this affords N-cyclopentenyl-lactam in racemic form. Given numerous uses related compounds, we were interested synthesis carbocylic nucleoside mimics. attempts results described herein.
sci-hub.se 参考文章(46)
Udo Nubbemeyer, Synthesis of Medium-Sized Ring Lactams ChemInform. ,vol. 33, pp. 125- 196 ,(2001) , 10.1007/3-540-44726-1_4
Andrew Abell, Advances in Amino Acid Mimetics and Peptidomimetics ,(1997)
Oliver Nayler, Martin Bolli, Boris Mathys, Beat Steiner, Claus Mueller, David Lehmann, Joerg Velker, Novel Thiophene Derivatives ,(2006)
Katsuhiko Hino, Jun-Ichi Matsumoto, Medicinal chemistry of 1-benzazepines Progress in Medicinal Chemistry. ,vol. 27, pp. 123- 141 ,(1990) , 10.1016/S0079-6468(08)70290-X
Omar Boutureira, M. Isabel Matheu, Yolanda Díaz, Sergio Castillón, Advances in the enantioselective synthesis of carbocyclic nucleosides Chemical Society Reviews. ,vol. 42, pp. 5056- 5072 ,(2013) , 10.1039/C3CS00003F
Phuong -T. Pham, Robert Vince, Carbovir-related compounds and phosphonate analogues Phosphorus Sulfur and Silicon and The Related Elements. ,vol. 182, pp. 779- 791 ,(2007) , 10.1080/10426500601047578
Angelica M. Meyer, Christopher E. Katz, Sze-Wan Li, David Vander Velde, Jeffrey Aubé, A tandem Prins/Schmidt reaction approach to marine alkaloids: formal and total syntheses of lepadiformines A and C. Organic Letters. ,vol. 12, pp. 1244- 1247 ,(2010) , 10.1021/OL100113R
Suresh E. Kurhade, Tanaji Mengawade, Debnath Bhuniya, Venkata P. Palle, D. Srinivasa Reddy, Synthesis of novel sugar-lactam conjugates using the Aubé reaction Organic and Biomolecular Chemistry. ,vol. 9, pp. 744- 747 ,(2011) , 10.1039/C0OB00719F
Kiran Sahasrabudhe, Vijaya Gracias, Kelly Furness, Brenton T. Smith, Christopher E. Katz, D. Srinivasa Reddy, Jeffrey Aubé, Asymmetric Schmidt reaction of hydroxyalkyl azides with ketones. Journal of the American Chemical Society. ,vol. 125, pp. 7914- 7922 ,(2003) , 10.1021/JA0348896
P.Andrews Evans, B. Holmes, Medium ring nitrogen heterocyles Tetrahedron. ,vol. 47, pp. 9131- 9166 ,(1991) , 10.1016/S0040-4020(01)96203-9