Absolute configuration assignment of 3-indolylacetate esters

Tetrahedron Asymmetry

Volumn 23, Issue 17, 2012, Pages 1279-1293

  Vázquez Arredondo, Rosa M ^a   Suárez Castillo, Oscar R ^a   Meléndez Rodríguez, Myriam ^a   Sánchez Zavala, Maricruz ^a   Cano Escudero, Indira C ^a   Bautista Hernández, Claudia I ^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 INDOLYL(BROMO)ACETATE; ACETIC ACID DERIVATIVE; ESTER DERIVATIVE; METHYL 3 (2 SEC BUTOXY 1 METHOXY 2 OXOETHYL) 1H INDOLE 1 CARBOXYLATE; METHYL 3 1 ETHOXY 2 [( 2 ISOPROPYL 5 METHYLCYCLOHEXYLOXY) 2 OXOETHYL] 1H INDOLE 1 CARBOXYLATE; METHYL 3 2 [( 2 ISOPROPYL 5 METHYLCYCLOHEXYLOXY) 1 MEETHOXY 2 OXOETHYL] 1H INDOLE 1 CARBOXYLATE; METHYL 3 [1 ISOPROPOXY 2 ( 2 ISOPROPYL 5 METHYLCYCLOHEXYLOXY) 2 OXOETHYL] 1H INDOLE 1 CARBOXYLATE; METHYL 3 [2 (2 ISOPROPYL 5 METHYLCYCLOHEXYLOXY) 1 (METHYLAMINO) 2 OXOETHYL] 1H INDOLE 1 CARBOXYLATE; METHYL 3 [2 (2 ISOPROPYL 5 METHYLCYCLOHEXYLOXYL) 1 (METHYLAMINO) 2 OXOETHYL] 1H INDOLE 1 CARBOXYLATE; UNCLASSIFIED DRUG;

ARTICLE; CIRCULAR DICHROISM; DENSITY FUNCTIONAL THEORY; METHODOLOGY; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOISOMERISM; VIBRATION; X RAY DIFFRACTION;

EID: 84867097170     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2012.08.005     Document Type: Article

References (29)

1. J.W. Mitchell, and P. Linder J. Agric. Food Chem. 10 1962 82 83
2. M. Katayama, Y. Kato, and S. Marumo Biosci. Biotechnol. Biochem. 68 2004 1287 2292
3. M. Katayama, Y. Kato, and S. Marumo Biosci. Biotechnol. Biochem. 65 2001 270 276
4. T. Hatano, M. Katayama, and S. Marumo Experientia 43 1987 1237 1239
5. O.R. Suárez-Castillo, M. Meléndez-Rodríguez, I.C. Cano-Escudero, S.L. De Ita-Gutiérrez, M. Sánchez-Zavala, M.S. Morales-Ríos, and P. Joseph-Nathan Heterocycles 81 2010 1169 1182
6. 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
7. O.R. Suárez-Castillo, M. Meléndez-Rodríguez, L.E. Castelán-Duarte, E. Zúñiga-Estrada, J. Cruz-Borbolla, M.S. Morales-Ríos, and P. Joseph-Nathan Tetrahedron: Asymmetry 22 2011 2085 2098
8. O.R. Suárez-Castillo, M. Meléndez-Rodríguez, L. Beiza-Granados, I.C. Cano-Escudero, M.S. Morales-Ríos, and P. Joseph-Nathan Nat. Prod. Commun. 6 2011 451 456
9. O.R. Suárez-Castillo, L.A. Montiel-Ortega, M. Meléndez- Rodríguez, and M. Sánchez-Zavala Tetrahedron Lett. 48 2007 17 20
10. 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
11. Sh.K. Latypov, J.M. Seco, E. Quiñoá, and R. Riguera J. Org. Chem. 60 1995 504 515
12. J.M. Seco, Sh.K. Latypov, E. Quiñoá, and R. Riguera Tetrahedron 53 1997 8541 8564
13. J.M. Seco, E. Quiñoá, and R. Riguera Chem. Rev. 104 2004 17 117
14. E.E. Kwan, and Sh.G. Huang Eur. J. Org. Chem. 2008 2671 2688
15. G. Chang, W.C. Guida, and W.C. Still J. Am. Chem. Soc. 111 1989 4379 4386
16. W.J. Hehre, L. Radom, P.v.R. Schleyer, and J.A. Pople Ab Initio Molecular Orbital Theory 1986 Wiley New York
17. N. Godbout, D.R. Salahub, J. Andzelm, and E. Wimmer Can. J. Chem. 70 1992 560 571
18. J. Andzelm, and E.J. Wimmer Chem. Phys. 96 1992 1280 1303
19. T.A.J. Halgren Comput. Chem. 17 1996 490 519
20. T.A.J. Halgren Comput. Chem. 17 1996 520 552
21. T.A.J. Halgren Comput. Chem. 17 1996 553 586
22. T.A. Halgren, and R.B.J. Nachbar Comput. Chem. 17 1996 587 615
23. T.A. Halgren J. Comput. Chem. 17 1996 616 641
24. As implemented in the computer package Spartan04, Windows v 1.0.1; Wavefunction Inc.: Irvine, CA, USA, 2004.
25. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Scalmani, G.; Barone, V.; Mennucci, B.; Petersson, G. A.; Nakatsuji, H.; Caricato, M.; Li, X.; Hratchian, H. P.; Izmaylov, A. F.; Bloino, J.; Zheng, G.; Sonnenberg, J. L.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Vreven, T.; Montgomery, J. A.; Peralta, J. E.; Ogliaro, F.; Bearpark, M.; Heyd, J. J.; Brothers, E.; Kudin, K. N.; Staroverov, V. N.; Kobayashi, R.; Normand, J.; Raghavachari, K.; Rendell, A.; Burant, J. C.; Iyengar, S. S.; Tomasi, J. Gaussian 09, ReVision A.02; Gaussian, Inc.: Wallingford, CT, 2009.
26. E. Debie, E. De Gussem, R.K. Dukor, W. Herrebout, L.A. Nafie, and P. Bultinck Chem. Phys. Chem. 12 2011 1542 1549
27. A. Zarei, A.R. Hajipour, and L. Khazdooz Synth. Commun. 41 2011 1772 1785
28. M.C. Burla, R. Caliandro, M. Camalli, B. Carrozzini, G.L. Cascarano, L. De Caro, C. Giacovazzo, G. Polidori, and R. Spagna J. Appl. Crystallogr. 38 2005 381 388
29. L.J. Farrugia J. Appl. Crystallogr. 32 1999 837 838