exo-2-oxazolidinone dienes in the total synthesis of the natural carbazoles, 6-methoxymurrayanine and clausenine

Synthesis

Volumn , Issue 13, 2007, Pages 1943-1948

  Bernal, Pablo ^a   Benavides, Adriana ^a   Bautista, Rafael ^a   Tamariz, Joaquín ^a  

^a INSTITUTO POLITÉCNICO NACIONAL   (Mexico)

Author keywords

4,5 dimethylene 2 oxazolidinone dienes; 6 methoxymurrayanine; Carbazoles; Clausenine; Decarbonylation; Diels Alder reaction

Indexed keywords

CARBAZOLES; CLAUSENINE; DECARBONYLATION; DIELS-ALDER REACTION; METHOXYMURRAYANINE; OXAZOLIDINONE DIENES;

AROMATIZATION; CYCLOADDITION; HYDROGENATION; METHYLATION; REGIOSELECTIVITY; SYNTHESIS (CHEMICAL);

OLEFINS;

3 (4 ANISYL) 4,5 DIMETHYLENE 1,3 OXAZOLIDIN 2 ONE; 6 METHOXYMURRAYANINE; ACROLEIN; ALKADIENE; CARBAZOLE DERIVATIVE; CLAUSENINE; EXO 2 OXAZOLIDINONE DIENE; LEWIS ACID; OXAZOLIDINE DERIVATIVE; UNCLASSIFIED DRUG;

AROMATIZATION; ARTICLE; CATALYSIS; CYCLOADDITION; DIELS ALDER REACTION; DRUG SYNTHESIS; HYDROGENATION; HYDROLYSIS; METHYLATION;

EID: 34447539978     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2007-983741     Document Type: Article

References (50)

1. For selected references, see: (a) Knölker, H.-J.; Reddy, K. R. Chem. Rev. 2002, 102, 4303; and references cited therein.
2. (b) Chakraborty, D. P.; Roy, S. In Progress in the Chemistry of Organic Natural Products, Vol. 57; Herz, W.; Grisebach, H.; Kirby, G. W.; Tamm, C., Eds.; Springer: Vienna, 1991, 71.
3. (c) Fiebig, M.; Pezzuto, J. M.; Soejarto, D. D.; Kinghorn, A. D. Phytochemistry 1985, 24, 3041.
4. (d) Chakraborty, D. P. Planta Med. 1980, 39, 97.
5. (e) Wu, T.-S.; Chan, Y.-Y.; Liou, M.-J.; Lin, F.-W.; Shi, L.-S.; Chen, K.-T. Phytother. Res. 1998, 12, S80.
6. (f) Bringmann, G.; Ledermann, A.; Holenz, J.; Kao, M.-T.; Busse, U.; Wu, H. G.; François, G. Planta Med. 1998, 64, 54.
7. (g) Wu, T.-S.; Huang, S.-C.; Wu, P.-L.; Teng, C.-M. Phytochemistry 1996, 43, 133.
8. (h) Chakraborty, A.; Chowdhury, B. K.; Bhattacharyya, P. Phytochemistry 1995, 40, 295.
9. (i) Chakraborty, A.; Saha, C.; Podder, G.; Chowdhury, B. K.; Bhattacharyya, P. Phytochemistry 1995, 38, 787.
10. (j) Bringmann, G.; Ledermann, A.; François, G. Heterocycles 1995, 40, 293.
11. (a) Chakraborty, D. P.; Bhattacharyya, P.; Roy, S.; Bhattacharyya, S. P.; Biswas, A. K. Phytochemistry 1978, 17, 834.
12. (b) Chowdhury, B. K.; Chakraborty, D. P. Chem. Ind. (London) 1969, 549.
13. (c) Wu, T.-S.; Huang, S.-C.; Wu, P.-L.; Kuoh, C.-S. Phytochemistry 1999, 52, 523.
14. (a) Chakraborty, D. P.; Barman, B. K.; Bose, P. K. Tetrahedron 1965, 21, 681.
15. (b) Bhattacharyya, P.; Chakraborty, D. P. Phytochemistry 1973, 12, 1831.
16. Chowdhury, B. K.; Chakraborty, D. P. Phytochemistry 1971, 10, 1967.
17. For selected and recent examples, see: (a) Pindur, U. Chimia 1990, 44, 406; and references cited therein.
18. (b) Beccalli, E.; Marchesini, A.; Pilati, T. Tetrahedron 1996, 52, 3029.
19. (c) Choshi, T.; Sada, T.; Fujimoto, H.; Nagayama, C.; Sugino, E.; Hibino, S. J. Org. Chem. 1997, 62, 2535.
20. (d) Lee, C.-Y.; Lin, C.-F.; Lee, J.-L.; Chiu, C.-C.; Lu, W.-D.; Wu, M.-J. J. Org. Chem. 2004, 69, 2106.
21. (e) Knölker, H.-J.; Schlechtingen, G. Heterocycles 2004, 63, 2393.
22. (f) Knölker, H.-J. Curr. Org. Synth. 2004, 1, 309.
23. (g) Appukkuttan, P.; Van der Eycken, E.; Dehaen, W. Synlett 2005, 127.
24. (h) Freeman, A. W.; Urvoy, M.; Criswell, M. E. J. Org. Chem. 2005, 70, 5014.
25. (i) Liu, C.-Y.; Knochel, P. Org. Lett. 2005, 7, 2543.
26. (j) Tsang, W. C. P.; Zheng, N.; Buchwald, S. L. J. Am. Chem. Soc. 2005, 127, 14560.
27. (k) Scott, T. L.; Yu, X.; Gorugantula, S. P.; Carrero-Martínez, G.; Söderberg, B. C. G. Tetrahedron 2006, 62, 10835.
28. (l) Kitawaki, T.; Hayashi, Y.; Ueno, A.; Chida, N. Tetrahedron 2006, 62, 6792.
29. For examples of synthesis of carbazoles 1-3, see: (a) Bringmann, G.; Tasler, S.; Endress, H.; Peters, K.; Peters, E.-M. Synthesis 1998, 1501.
30. (b) Chakraborty, D. P.; Chowdhury, B. K. J. Org. Chem. 1968, 33, 1265.
31. (c) Knölker, H.-J.; Bauermeister, M. Tetrahedron 1993, 48, 11221.
32. (d) Kuwahara, A.; Nakano, K.; Nozaki, K. J. Org. Chem. 2005, 70, 413.
33. (e) Mal, D.; Senapati, B.; Pahari, P. Tetrahedron Lett. 2006, 47, 1071.
34. (f) Knölker, H.-J.; Wolpert, M. Tetrahedron 2003, 59, 5317.
35. (g) Brenna, E.; Fuganti, C.; Serra, S. Tetrahedron 1998, 54, 1585.
36. Mandal, A. B.; Delgado, F.; Tamariz, J. Synlett 1998, 87.
37. (a) Zempoalteca, A.; Tamariz, J. Heterocycles 2002, 57, 259.
38. (b) Benavides, A.; Peralta, J.; Delgado, F.; Tamariz, J. Synthesis 2004, 2499.
39. (a) Hernández, R.; Sánchez, J. M.; Gómez, A.; Trujillo, G.; Aboytes, R.; Zepeda, G.; Bates, R. W.; Tamariz, J. Heterocycles 1993, 36, 1951.
40. (b) Mandal, A. B.; Gómez, A.; Trujillo, G.; Méndez, F.; Jiménez, H. A.; Rosales, M. J.; Martínez, R.; Delgado, F.; Tamariz, J. J. Org. Chem. 1997, 62, 4105.
41. Li, W.-S.; McChesney, J. D.; El-Feraly, F. S. Phytochemistry 1991, 30, 343.
42. Hamza, O. J. M.; van den Bout-van den Beukel, C. J. P.; Matee, M. I. N.; Moshi, M. J.; Mikx, F. H. M.; Selemani, H. O.; Mbwambo, Z. H.; Van der Ven, A. J. A. M.; Verweij, P. E. J. Ethnopharmacol. 2006, 108, 124.
43. For a preliminary report, see: González-Romero, C.; Bernal, P.; Jiménez, F.; Cruz, M. C.; Fuentes-Benites, A.; Benavides, A.; Bautista, R.; Tamariz, J. Pure Appl. Chem. 2007, 79, 181.
44. Fuentes, A.; Martínez-Palou, R.; Jiménez-Vázquez, H. A.; Delgado, F.; Reyes, A.; Tamariz, J. Monatsh. Chem. 2005, 136, 177.
45. (a) Åkermark, B.; Eberson, E.; Jonsson, E.; Pettersson, E. J. Org. Chem. 1975, 40, 1365.
46. (b) Liu, G.; Zhang, A. Tetrahedron Lett. 1999, 40, 341.
47. (a) Smolík, J.; Kraus, M. Collect. Czech. Chem. Commun. 1972, 37, 3042.
48. (b) Demopoulos, B. J.; Anderson, H. J.; Loader, C. E.; Faber, K. Can. J. Chem. 1983, 61, 2415.
49. (c) Peroutková, V.; Beránek, L. Collect. Czech. Chem. Commun. 1976, 41, 526.
50. (d) Lejemble, P.; Maire, Y.; Gaset, A.; Kalck, P. Chem. Lett. 1983, 1403.