Absolute configuration assignment of 3-oxindolylacetyl-4- phenyloxazolidinone derivatives

Tetrahedron Asymmetry

Volumn 22, Issue 24, 2011, Pages 2085-2098

  Suárez Castillo, Oscar R ^a   Meléndez Rodríguez, Myriam ^a   Castelán Duarte, Luis E ^a   Zúñiga Estrada, Erick A ^a   Cruz Borbolla, Julián ^a   Morales Ríos, Martha S ^b   Joseph Nathan, Pedro ^b  

^a UNIVERSIDAD AUTÓNOMA DEL ESTADO DE HIDALGO   (Mexico)

^b DEPARTAMENTO DE FÍSICA   (Mexico)

Author keywords

[No Author keywords available]

Indexed keywords

3 [2 (1,3 DIMETHYL 2 OXOINDOLIN 3 YL)ACETYL] 4 PHENYLOXAZOLIDIN 2 ONE; 3 [2 (3 BENZYL 1 METHYL 2 OXOINDOLIN 3 YL)ACETYL] 4 PHENYLOXAZOLIDIN 2 ONE; 3 [2 (3 METHYL 2 OXO 1 PHENYLINDOLIN 3 YL)ACETYL] 4 PHENYLOXAZOLIDIN 2 ONE; 3 [2 [1 BENZYL 3 (3 METHYLBUT 2 ENYL) 2 OXOINDOLIN 3 YL]ACETYL] 4 PHENYLOXAZOLIDIN 2 ONE; 3 [2 [1,3 BIS(3 METHYLBUT 2 ENYL) 2 OXOINDOLIN 3 YL]ACETYL] 4 PHENYLOXAZOLIDIN 2 ONE; 3 OXINDOLYLACETYL 4 PHENYLOXAZOLIDINONE DERIVATIVE; OXAZOLIDINONE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CIRCULAR DICHROISM; DENSITY FUNCTIONAL THEORY; DIASTEREOISOMER; DRUG CONFORMATION; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; VALIDATION STUDY; X RAY DIFFRACTION;

EID: 84856390741     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2011.11.018     Document Type: Article

References (61)

1. H. Kinashi, Y. Suzuki, S. Takeuchi, and A. Kawarada Agric. Biol. Chem. 40 1976 2465 2470
2. Y. Suzuki, H. Kinashi, S. Takeuchi, and A. Kawarada Phytochemistry 16 1977 635 637
3. T. Ohmoto, K. Yamaguchi, and K. Ikeda Chem. Pharm. Bull. 36 1988 578 581
4. T.G. Dekker, T.G. Fourie, E. Matthee, and F.O. Snyckers Phytochemistry 26 1987 1845 1846
5. K. Monde, K. Sasaki, A. Shirata, and M. Takasugi Phytochemistry 30 1991 2915 2917
6. H.-p. Zhang, Y. Kamano, Y. Ichihara, H. Kizu, K. Komiyama, H. Itokawa, and G.R. Pettit Tetrahedron 51 1995 5523 5528
7. A. Fréchard, N. Fabre, C. Péan, S. Montaut, M.-T. Fauvel, P. Rollin, and I. Fourasté Tetrahedron Lett. 42 2001 9015 9017
8. T. Emura, T. Esaki, K. Tachibana, and M. Shimizu J. Org. Chem. 71 2006 8559 8564
9. M.S. Morales-Ríos, O.R. Suárez-Castillo, and P. Joseph-Nathan Trends Heterocycl. Chem. 6 1999 111 124
10. S. Horne, N. Taylor, S. Collins, and R. Rodrigo J. Chem. Soc., Perkin Trans. 1 1991 3047 3051
11. Q.-s. Yu, W.-m. Luo, and Y.-q. Li Heterocycles 36 1993 1279 1285
12. M. Pallavicini, E. Valoti, L. Villa, and I. Resta Tetrahedron: Asymmetry 5 1994 363 370
13. X.-F. Pei, and S. Bi Heterocycles 39 1994 357 360
14. T. Matsuura, L.E. Overman, and D.J. Poon J. Am. Chem. Soc. 120 1998 6500 6503
15. M.S. Morales-Ríos, and O.R. Suárez-Castillo Nat. Prod. Commun. 3 2008 629 642
16. T. Kawasaki, R. Terashima, K.-e. Sakaguchi, H. Sekiguchi, and M. Sakamoto Tetrahedron Lett. 37 1996 7525 7528
17. M.S. Morales-Ríos, E. Rivera-Becerril, and P. Joseph-Nathan Tetrahedron: Asymmetry 16 2005 2493 2499
18. O.R. Suárez-Castillo, M. Sánchez-Zavala, M. Meléndez-Rodríguez, L.E. Castelán-Duarte, M.S. Morales-Ríos, and P. Joseph-Nathan Tetrahedron 62 2006 3040 3051
19. O.R. Suárez-Castillo, M. Sánchez-Zavala, M. Meléndez-Rodríguez, E. Aquino-Torres, M.S. Morales-Ríos, and P. Joseph-Nathan Heterocycles 71 2007 1539 1551
20. T. Kawasaki, M. Shinada, D. Kamimura, M. Ohzono, and A. Ogawa Chem. Commun. 2006 420 422
21. O.R. Suárez-Castillo, M. Meléndez-Rodríguez, L.E. Castelán-Duarte, M. Sánchez-Zavala, E. Rivera-Becerril, M.S. Morales-Ríos, and P. Joseph-Nathan Tetrahedron: Asymmetry 20 2009 2374 2389
22. T. Kouko, K. Matsumura, and T. Kawasaki Tetrahedron 61 2005 2309 2318
23. L.W. Boteju, K. Wegner, X. Qian, and J.V. Hruby Tetrahedron 50 1994 2391 2404
24. S.G. Davies, and H.J. Sanganee Tetrahedron: Asymmetry 6 1995 671 674
25. C. Palomo, J.M. Aizpurua, A. Mielgo, and A. Linden J. Org. Chem. 61 1996 9186 9195
26. T. Hosokawa, T. Yamanaka, M. Itotani, and S.-I. Murahashi J. Org. Chem. 60 1995 6159 6167
27. T. Akiba, O. Tamura, M. Hashimoto, Y. Kobayashi, T. Katoh, K. Nakatani, M. Kamada, I. Hayakawa, and S. Terashima Tetrahedron 50 1994 3905 3914
28. I.W. Davies, C.H. Senanayake, L. Castonguay, R.D. Larsen, T.R. Verhoeven, and P.J. Reider Tetrahedron Lett. 36 1995 7619 7622
29. W.H. Pirkle, and K.A. Simmons J. Org. Chem. 48 1983 2520 2527
30. L.N. Pridgen, and C. De Brosse J. Org. Chem. 62 1997 216 220
31. M.S. Morales-Ríos, E. Rivera-Becerril, D.E. González- Juárez, J.B. García-Vázquez, J.J. Trujillo-Serrato, A. Hernández-Barragán, and P. Joseph-Nathan Nat. Prod. Commun. 6 2011 457 464
32. G. Lakshmaiah, T. Kawabata, M. Shang, and K. Fuji J. Org. Chem. 64 1999 1699 1704
33. H. Miyamoto, Y. Okawa, A. Nakazaki, and S. Kobayashi Tetrahedron Lett. 48 2007 1805 1808
34. G.N. Walker, D. Alkalay, and R.T. Smith J. Org. Chem. 30 1965 2973 2983
35. B.M. Trost, J.L. Belletire, S. Godleski, P.G. McDougal, and J.M. Balkovec J. Org. Chem. 51 1986 2370 2374
36. K. Hori, N. Hikage, A. Inagaki, S. Mori, K. Nomura, and E. Yoshii J. Org. Chem. 57 1992 2888 2902
37. T. Yabuuchi, and T. Kusumi J. Org. Chem. 65 2000 397 404
38. N.A. Shaye, and J. Eames Tetrahedron Lett. 51 2010 5892 5895
39. F.H. Osman, and F.A. El-Samahy Phosphorus, Sulfur Silicon 134/135 1998 437-446
40. Aldrich/ACD Library of FT NMR Spectra Pro. Advanced Chemistry Development, Inc. and Aldrich Chemical Company, Inc. V. 1.00, 1998.
41. R.H. Taaning, K.B. Lindsay, B. Schiøtt, K. Daasbjerg, and T. Skrydstrup J. Am. Chem. Soc. 131 2009 10253 10262
42. S. Kitoh, H. Senda, K.-K. Kunimoto, S. Maeda, A. Kuwae, and K. Hanai Cryst. Res. Technol. 39 2004 375 381
43. G. Chang, W.C. Guida, and W.C. Still J. Am. Chem. Soc. 111 1989 4379 4386
44. W.J. Hehre, L. Radom, P.v.R. Schleyer, and J.A. Pople Ab Initio Molecular Orbital Theory 1986 Wiley New York
45. N. Godbout, D.R. Salahub, J. Andzelm, and E. Wimmer Can. J. Chem. 70 1992 560 571
46. J. Andzelm, and E. Wimmer J. Chem. Phys. 96 1992 1280 1303
47. J.R. Cheeseman, G.W. Trucks, T.A. Keith, and M.J. Frisch J. Chem. Phys. 104 1996 5497 5509
48. C.M. Cerda-García-Rojas, C.A.N. Catalán, A.C. Muro, and P. Joseph-Nathan J. Nat. Prod. 71 2008 967 971
49. T.A. Halgren J. Comput. Chem. 17 1996 490 519
50. T.A. Halgren J. Comput. Chem. 17 1996 520 552
51. T.A. Halgren J. Comput. Chem. 17 1996 553 586
52. T.A. Halgren, and R.B. Nachbar J. Comput. Chem. 17 1996 587 615
53. T.A. Halgren J. Comput. Chem. 17 1996 616 641
54. As implemented in the computer package spartan04, Windows v 1.0.1; Wavefunction Inc.: Irvine, CA, USA, 2004.
55. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery, J. A., Jr.; Vreven, T.; Kudin, K. N.; Burant, J. C.; Millam, J. M.; Iyengar, S. S.; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson, G. A.; Nakatsuji, H.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Klene, M.; Li, X.; Knox, J. E.; Hratchian, H. P.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Ayala, P. Y.; Morokuma, K.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Zakrzewski, V. G.; Dapprich, S.; Daniels, A. D.; Strain, M. C.; Farkas, O.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Ortiz, J. V.; Cui, Q.; Baboul, A. G.; Clifford, S.; Cioslowski, J.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Gonzalez, C.; Pople, J. A.; Gaussian, Inc.: Wallingford CT, 2004.
56. T. Kawasaki, M. Shinada, M. Ohzono, A. Ogawa, R. Terashima, and M. Sakamoto J. Org. Chem. 73 2008 5959 5964
57. A. Nakahashi, Y. Yaguchi, N. Miura, M. Emura, and K. Monde J. Nat. Prod. 74 2011 707 711
58. L.G. Zepeda, E. Burgueño-Tapia, and P. Joseph-Nathan Nat. Prod. Commun. 6 2011 429 432
59. E. Debie, E. De Gussem, R.K. Dukor, W. Herrebout, L.A. Nafie, and P. Bultinck Chem. Phys. Chem. 12 2011 1542 1549
60. G.M. Sheldrick Programs for Crystal Structure Analysis 1988 Institüt für Anorganische Chemie der Universität, University of Göttingen Göttingen, Germany
61. L.J. Farrugia J. Appl. Crystallogr. 32 1999 837 838