Synthesis of 2-aryloxypropanoic acids analogues of clofibric acid and assignment of the absolute configuration by 1H NMR spectroscopy and DFT calculations

Tetrahedron Asymmetry

Volumn 19, Issue 8, 2008, Pages 989-997

  Ammazzalorso, Alessandra ^a   Bettoni, Giancarlo ^a   De Filippis, Barbara ^a   Fantacuzzi, Marialuigia ^a   Giampietro, Letizia ^a   Giancristofaro, Antonella ^a   Maccallini, Cristina ^a   Re, Nazzareno ^a   Amoroso, Rosa ^a   Coletti, Cecilia ^a  

^a UNIVERSITY OF CHIETI   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

2 OXYPROPANOIC ACID; CARBOXYLIC ACID; CLOFIBRIC ACID; EFLOXATE; MANDELIC ACID; PROPIONIC ACID DERIVATIVE;

ARTICLE; CALCULATION; CHIRALITY; CONFORMATIONAL TRANSITION; DENSITY FUNCTIONAL THEORY; DIASTEREOISOMER; DRUG SYNTHESIS; ENANTIOSELECTIVITY; ENERGY YIELD; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE;

EID: 43149088468     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2008.04.010     Document Type: Article

References (27)

1. Seco J.M., Ortiz A., Quiñoá E., and Riguera R. Chem. Rev. 104 (2004) 17-118
2. Wenzel T.J., and Wilcox J.D. Chirality 15 (2003) 256-270
3. Seco J.M., Quiñoá E., and Riguera R. Tetrahedron: Asymmetry 12 (2001) 2915-2925
4. Porto S., Seco J.M., Ortiz A., Quiñoá E., and Riguera R. Org. Lett. 9 (2007) 5015-5018
5. Ferreiro M.J., Latypov Sh.K., Quiñoá E., and Riguera R. J. Org. Chem. 65 (2000) 2658-2666
6. Iwamoto H., Kobayashi Y., Kawatani T., Suzuki M., and Fukazawa Y. Tetrahedron Lett. 47 (2006) 1519-1523
7. Latypov Sh.K., Seco J.M., Quiñoá E., and Riguera R. J. Org. Chem. 60 (1995) 504-515
8. Seco J.M., Latypov Sh.K., Quiñoá E., and Riguera R. Tetrahedron 53 (1997) 8541-8564
9. Seco J.M., Quiñoá E., and Riguera R. J. Org. Chem. 6 (1997) 7569-7574
10. Trost B.M., Bunt R.C., and Pulley S.R. J. Org. Chem. 59 (1994) 4202-4205
11. Latypov Sh.K., Seco J.M., Quiñoá E., and Riguera R. J. Org. Chem. 60 (1995) 1538-1545
12. Lopez B., Quiñoá E., and Riguera R. J. Am. Chem. Soc. 121 (1999) 9724-9725
13. Yabuuchi T., and Kusumi T. J. Org. Chem. 65 (2000) 397-404
14. Ichikawa A., Ono H., Hiradate S., Watanabe M., and Harada N. Tetrahedron: Asymmetry 13 (2002) 1167-1172
15. Tyrrell E., Tsang M.W.H., Skinner G.A., and Fawcett J. Tetrahedron 52 (1996) 9841-9852
16. Staels B., Dallongeville J., Auwerx J., Schoonjans K., Leitersdorf E., and Fruchart J.-C. Circulation 98 (1998) 2088-2093
17. Chapman M.J. Atherosclerosis 171 (2003) 1-13
18. Brown P.J., Winegar D.A., Plunket K.D., Moore L.B., Lewis M.C., Wilson J.G., Sundseth S.S., Koble C.S., Wu Z., Chapman J.M., Lehmann J.M., Kliewer S.A., and Willson T.M. J. Med. Chem. 42 (1999) 3785-3788
19. Shi G.Q., Dropinski J.F., Zhang Y., Santini C., Sahoo S.P., Berger J.P., MacNaul K.L., Zhou G., Agrawal A., Alvaro R., Cai T., Hernandez M., Wright S.D., Moller D.E., Heck J.V., and Meinke P.T. J. Med. Chem. 48 (2005) 5589-5599
20. Sauerberg P., Mogensen J.P., Jeppesen L., Bury P.S., Fleckner J., Olsen G.S., Jeppesen C.B., Wulff E.M., Pihera P., Havranek M., Polivka Z., and Pettersson I. Bioorg. Med. Chem. Lett. 17 (2007) 3198-3202
21. Yamazaki Y., Abe K., Toma T., Nishikawa M., Ozawa H., Okuda A., Araki T., Oda S., Inoue K., Shibuya K., Staels B., and Fruchart J.-C. Bioorg. Med. Chem. Lett. 17 (2007) 4689-4693
22. Mitsunobu O. Synthesis 1 (1981) 1-28
23. Klyne W., and Prelog V. Experientia 16 (1960) 521-523
24. Kane S., and Hersh W.H. J. Chem. Educ. 77 (2000) 1366
25. macromodel, Version 9.0; Schrödinger, LLC: New York, NY, 2005.
26. Macromodel xcluster, Version 9.0; Schrödinger, LLC: New York, NY, 2005.
27. jaguar, Version 6.0; Schrödinger, LLC: New York, NY, 2005.