Highly diastereoselective synthesis of new heterolignan-like 6,7-methylendioxy-tetrahydroquinolines using the clove bud essential oil as raw material

Tetrahedron Letters

Volumn 52, Issue 12, 2011, Pages 1388-1391

  Merchan Arenas, Diego R ^a   Rojas Ruíz, Fernando A ^a   Kouznetsov, Vladimir V ^a  

^a UNIVERSIDAD INDUSTRIAL DE SANTANDER   (Colombia)

Author keywords

[No Author keywords available]

Indexed keywords

6,7 METHYLENDIOXY TETRAHYDROQUINOLINE DERIVATIVE; ESSENTIAL OIL; EUGENOL; ISOEUGENOL; LIGNAN DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CLOVE; FLOWER; ISOMERIZATION; RACEMIC MIXTURE; SYNTHESIS;

SYZYGIUM AROMATICUM;

EID: 79951768335     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2011.01.083     Document Type: Article

References (43)

1. Corma, A.; Iborra, S.; Velty, A. Chem. Rev. 2007, 107, 2411.
2. (a) Kouznetsov, V. V.; Bohórquez Romero, A. R.; Stashenko, E. E. Tetrahedron Lett. 2007, 48, 8855;
3. (b) Kouznetsov, V. V.; Merchan Arenas, D. R.; Bohórquez Romero, A. R. Tetrahedron Lett. 2008, 49, 3097.
4. (a) Jacquemond-Collet, I.; Benoit-Vical, F.; Mustofa, V.; Stanislas, A.; Mallié, E.; Fourasté, I. Planta Med. 2002, 68, 68;
5. (b) Wallace, O. B.; Lauwers, K. S.; Jones, S. A.; Dodge, J. A. Bioorg. Med. Chem. Lett. 2003, 13, 1907;
6. (c) Dorey, G.; Lockhart, B.; Lestage, P.; Casara, P. Bioorg. Med. Chem. Lett. 2000, 10, 935.
7. Jaquemond-Collet, I.; Hannedouche, S.; Fabre, N.; Fourasté, I.; Moulis, C. Phytochemistry 1999, 51, 1167.
8. Kam, T.-S.; Subramaniam, G.; Lim, T.-M. Tetrahedron Lett. 2001, 42, 5977.
9. (a) Da Silva Filho, A. A.; Tomazela, D. M.; Albuquerque, S.; Bastos, J. K.; E Silva, M. L. A.; Eberlin, M. N. J. Nat. Prod. 2004, 67, 42;
10. (b) Cutillo, F.; D'abrosca, B.; Fiorentino, A.; Dellagreca, M.; Zarrelli, A. J. Agric. Food. Chem. 2003, 51, 6165;
11. (c) Salemm, M.; Kim, H.; Ali, M.; Lee, Y. Nat. Prod. Rep. 2005, 22, 696;
12. (d) Kwon, H. S.; Kim, M.-J.; Jeong, H. J.; Yang, M. S.; Park, K. H.; Jeong, T.-S.; Lee, W. S. Bioorg. Med. Chem. Lett. 2008, 18, 194.
13. (a) Gordaliza, M.; García, P. A.; Miguel del Corral, J. M.; Castro, M. A.; Gómez- Zurita, M. A. Toxicon 2004, 44, 441;
14. (b) Apers, S.; Vietinck, A.; Pieters, L. Phytochem. Rev. 2003, 2, 201;
15. (c) Sick Woo, W.; Hyun Shin, K.; Wagner, H.; Lotter, H. Phytochemistry 1987, 26, 1542.
16. (a) Moss, G. P. Pure Appl. Chem. 2000, 72, 1493;
17. (b) Frackenpohla, J.; Adeltb, I.; Antonicekb, H.; Arnoldb, C.; Behrmannb, P.; Blahaa, N.; Böhmerb, J.; Gutbrodb, O.; Hankeb, R.; Hohmanna, S.; van Houtdreveb, M.; Löselb, P.; Malsamb, O.; Melchersb, M.; Neufertb, V.; Peschela, E.; Reckmannb, U.; Schenkeb, T.; Thiesenb, H.; Veltenb, R.; Vogelsangb, K.; Weissc, H. Bioorg. Med. Chem. 2009, 17, 4160;
18. (c) Ramos, A. C.; Peláez-Lamamié de Clairac, R.; Medarde, M. Heterocycles 1999, 51, 1443.
19. (a) Medarde, M.; Ramos, A. C.; Caballero, E.; López, J.; Peláez-Lamamié de Clairac, R.; San Feliciano, A. Tetrahedron Lett. 1998, 39, 2001;
20. (b) Ramos, A. C.; Peláez, R.; López, J.; Caballero, E.; Medarde, M.; San Feliciano, A. Tetrahedron 2001, 57, 3963.
21. Madrigal, B.; Puebla, P.; Peláez, R.; Caballero, E.; Medarde, M. J. Org. Chem. 2003, 68, 854.
22. (a) Leteurtre, F.; Madalengoitia, J.; Orr, A.; Guzi, T.; Lehnert, E.; MacDonald, T.; Pommier, Y. Cancer Res. 1992, 52, 4478;
23. (b) Madalengoitia, J. S.; Tepe, J. J.; Werbovetz, K. W.; Lehnert, E. K.; MacDonald, T. L. Bioorg. Med. Chem. 1997, 5, 1807;
24. (c) Tepe, J. J.; Madalengoitia, J. S.; Slunt, K. M.; Werbovetz, K. W.; Spoors, P. G.; Macdonald, T. L. J. Med. Chem. 1996, 39, 2188.
25. (a) Hajbi, Y.; Neagoie, C.; Biannic, B.; Chilloux, A.; Vedrenne, E.; Baldeyrou, B.; Bailly, C.; Mérour, J.-Y.; Rosca, S.; Routier, S.; Lansiaux, A. Eur. J. Med. Chem. 2010, 45, 5428;
26. (b) Muhuhi, J.; Spaller, M. R. J. Org. Chem. 2006, 71, 5515.
27. See review, (a) Kouznetsov, V. V. Tetrahedron 2009, 65, 2721. and references cited therein; Recent works:
28. (b) Smith, C.; Gavrilyuk, J.; Lough, A.; Batey, R. J. Org. Chem. 2010, 75, 702;
29. (c) Subba Reddy, B. V.; Grewal, H. Tetrahedron Lett. 2010. doi:10.1016/j.tetlet.2010.12.003;
30. (d) Vicente-García, E.; Catti, F.; Ramón, R.; Lavilla, R. Org. Lett. 2010, 12, 860.
31. (a) Lopez-Perez, J.; Abad, A.; del Olmo, E.; San Feliciano, A. Tetrahedron 2006, 62, 2370;
32. (b) Wang, E.-C.; Wein, Y.-S.; Kuo, Y.-H. Tetrahedron Lett 2006, 47, 9195;
33. (c) Angle, S. R.; Arnaiz, D. J. Org. Chem. 1992, 57, 5937.
34. Jana, G. P.; Ghorai, B. K. Tetrahedron 2007, 63, 12015.
35. Hajbi, Y.; Neagoie, C.; Biannic, B.; Chilloux, A.; Vedrenne, E.; Baldeyrou, B.; Bailly, C.; Mérour, J.-Y.; Rosca, S.; Routier, S.; Lansiau, A. Eur. J. Med. Chem. 2010, 45, 5428.
36. Employing as characterizing criteria, data system ChemStation G17001DA and its data base (NIST 2002, NBS 75K and WILEY 138K). See Supplementary data.
37. Srivastava, V. K.; Bajaj, H. C.; Jasra, R. V. Catal. Commun. 2003, 543.
38. The reaction crude analyzed by GC - MS showed a relative area with 50.5% of cis/trans-isoeugenol with 6:1 trans/cis ratio. This mixture was employed without any purification.
39. Khadem, S.; Udachin, K. A.; Enright, G. D.; Prakesch, M.; Arya, P. Tetrahedron Lett. 2009, 50, 6661.
40. Ishihara, Y.; Kiyota, Y.; Goto, G. Chem. Pharm. Bull. 1990, 38, 3024.
41. Sui, Z. H.; Altom, J.; Nguyen, V.; Fernandez, J.; Bernstein, J. I.; Hiliard, J. J.; Barrett, J. F.; Podlogar, B. L.; Ohemeng, K. A. Bioorg. Med. Chem. 1998, 6, 735.
42. (a) Kouznetsov, V. V.; Merchan Arenas, D. R.; Arvelo, F.; Bello Forero, J. S.; Sojo, F.; Muñoz, A. Lett. Drug Des Discov 2010, 7, 632;
43. (b) Muñoz, A.; Sojo, F.; Merchan Arenas, D.; Kouznetsov, V. V.; Arvelo, F. Chem.-Biol. Interact. 2011. doi:10.1016/j.cbi.2010.11.010.