Expedient Pathway into Optically Active 2-Oxopiperidines

作者: Sebastiaan Bas A. M. W. van den Broek , Peter G. W. Rensen , Floris L. van Delft , Floris P. J. T. Rutjes

DOI: 10.1002/EJOC.201000587

关键词: ChemistryPiperidineRing (chemistry)Ring-closing metathesisOrganic chemistryGeneral interestMetathesisChemical synthesisOptically activeCyclic compoundPhysical and Theoretical Chemistry

摘要: The piperidine ring system is one of the most common structural subunits and found in many natural products. Moreover, alkaloids derivatives thereof are great interest for pharmaceutical industry since they exhibit a wide range biological activities. Consequently, short valuable routes to highly functionalized building blocks this important general interest. A ring-closing metathesis (RCM)-mediated approach based on linear (substituted) dehydroamino esters was developed provide cyclic esters. These structures represent intermediates en route substituted pipecolic acids as well more elaborate heterocycles.

参考文章(61)
D Lamarre, G Croteau, E Wardrop, L Bourgon, D Thibeault, C Clouette, M Vaillancourt, E Cohen, C Pargellis, C Yoakim, P C Anderson, Antiviral properties of palinavir, a potent inhibitor of the human immunodeficiency virus type 1 protease. Antimicrobial Agents and Chemotherapy. ,vol. 41, pp. 965- 971 ,(1997) , 10.1128/AAC.41.5.965
C R Salhoff, D M Zimmerman, J D Leander, P L Ornstein, D D Schoepp, S Zeman, D Lodge, Pharmacological characterization of LY233053: A structurally novel tetrazole-substituted competitive N-methyl-D-aspartic acid antagonist with a short duration of action Journal of Pharmacology and Experimental Therapeutics. ,vol. 255, pp. 1301- 1308 ,(1990)
F. Javier Sardina, Henry Rapoport, Enantiospecific Synthesis of Heterocycles from α-Amino Acids Chemical Reviews. ,vol. 96, pp. 1825- 1872 ,(1996) , 10.1021/CR9300348
Yoshitaka Ichikawa, Yasuhiro Igarashi, Mie Ichikawa, Yoshitomo Suhara, 1-N-Iminosugars: Potent and Selective Inhibitors of β-Glycosidases Journal of the American Chemical Society. ,vol. 120, pp. 3007- 3018 ,(1998) , 10.1021/JA973443K
Ramaiah Kumareswaran, Alfred Hassner, Asymmetric syntheses of N-acetyl-(R)-coniine and N-Boc-(2R,6R)-solenopsin A via ring-closing metathesis Tetrahedron-asymmetry. ,vol. 12, pp. 2269- 2276 ,(2001) , 10.1016/S0957-4166(01)00411-6
Yasunori Banba, Chiemi Abe, Hideo Nemoto, Atsushi Kato, Isao Adachi, Hiroki Takahata, Asymmetric synthesis of fagomine and its congeners Tetrahedron-asymmetry. ,vol. 12, pp. 817- 819 ,(2001) , 10.1016/S0957-4166(01)00136-7
David Bensa, Iain Coldham, Pia Feinäugle, Ravindra B. Pathak, Roger J. Butlin, Synthesis of carboxylic amides by ring-opening of oxazolidinones with Grignard reagents Organic and Biomolecular Chemistry. ,vol. 6, pp. 1410- 1415 ,(2008) , 10.1039/B800849C
Panolil C. Raveendranath, Vincent J. Blazis, Kwasi Agyei-Aye, Anna K. Hebbler, Lisa N. Gentile, Elma S. Hawkins, Stephen C. Johnson, David C. Baker, A synthetic route to 3-C-alkyl (or 3-C-phenyl-) 2,3-dideoxy-d-erythro-pentono-1,4-lactones: intermediates in the synthesis of 2(3H)-furanones Carbohydrate Research. ,vol. 253, pp. 207- 223 ,(1992) , 10.1016/0008-6215(94)80066-9
Tobias Hoffmann, Reiner Waibel, Peter Gmeiner, A general approach to dehydro-Freidinger lactams: ex-chiral pool synthesis and spectroscopic evaluation as potential reverse turn inducers. Journal of Organic Chemistry. ,vol. 68, pp. 62- 69 ,(2003) , 10.1021/JO0261653