Epoxides, cyclic sulfites, and sulfate from natural pentacyclic triterpenoids: Theoretical calculations and chemical transformations

Journal of Organic Chemistry

Volumn 68, Issue 12, 2003, Pages 4833-4844

  García Granados, Andrés ^a   López, Pilar E ^a   Melguizo, Enrique ^a   Moliz, Juan N ^a   Parra, Andrés ^a   Simeó, Yolanda ^a   Dobado, José A ^b  

^a UNIVERSITY OF GRANADA   (Spain)

^b UNIVERSITY OF GRANADA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

CARBOXYLIC ACIDS; PROBABILITY DENSITY FUNCTION; SYNTHESIS (CHEMICAL); X RAY ANALYSIS;

COUPLING CONSTANTS;

DERIVATIVES;

EPOXIDE; HALOGEN; HETEROCYCLIC COMPOUND; MASLINIC ACID; SULFATE; SULFITE; SULFUR DERIVATIVE; TRITERPENE DERIVATIVE; TRITERPENOID;

ARTICLE; BECKMANN REARRANGEMENT; BIOTRANSFORMATION; CALCULATION; CARBON NUCLEAR MAGNETIC RESONANCE; CRYSTAL STRUCTURE; OZONOLYSIS; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

AZA COMPOUNDS; CRYSTALLOGRAPHY, X-RAY; CYCLIZATION; EPOXY COMPOUNDS; MODELS, THEORETICAL; MOLECULAR STRUCTURE; OLEANOLIC ACID; STEREOISOMERISM; SULFATES; SULFITES; TRITERPENES;

EID: 0037941123     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo026832s     Document Type: Article

References (39)

1. (a) Dictionary of Natural Products on CD-ROM, ISSN 0966-2146 ver. 5:1; Chapman & Hall: New York, 1996; oleanolic acid, CAS [508-02-1]; maslinic acid, CAS [4373-41-5].
2. (b) Phytochemical and Ethnobotanical DB. http://www.ars-grin.gov/duke/plants.html.
3. García-Granados, A.; Martínez, A.; Parra, A.; Rivas, F. PCT Int. Appl. W0 98 04331, 1998; Chem. Abstr. 1998, 128, 179706.
4. (a) Liu, J. Ethnopharmacology 1995, 49, 57.
5. (b) Assefa, H.; Nimrod, A.; Walker, L.; Sindelar, R. Bioorg. Med. Chem. Lett. 2001, 11, 619.
6. (c) Honda, T.; Rounds, B. V.; Bore, L.; Finlay, H. J.; Favaloro, F. G., Jr.; Suh, N.; Wang, Y.; Sporn, M. B.; Gribble, G. W. J. Med. Chem. 2000, 43, 4233.
7. (a) Kashiwada, Y.; Ikeshiro, Y.; Nagao, T.; Okabe, H.; Cosentino, L. M.; Lee, K. H. J. Nat. Prod. 2000, 63, 1619.
8. (b) Mengoni, F.; Lichtner, M.; Battinelli, L.; Marzi, M.; Mastroianni, C. M.; Vullo, V.; Mazzanti, G. Planta Med. 2002, 68, 111.
9. For a review on cyclic sulfites and cyclic sulfates, see: (a) Lohray, B. B. Synthesis 1992, 1035. (b) Byun, H. S.; He, L.; Bittman, R. Tetrahedron 2000, 56, 7051.
10. For a review on cyclic sulfites and cyclic sulfates, see: (a) Lohray, B. B. Synthesis 1992, 1035. (b) Byun, H. S.; He, L.; Bittman, R. Tetrahedron 2000, 56, 7051.
11. (a) Sharpless, K. B.; Kim, B. M. Tetrahedron Lett. 1989, 30, 655.
12. (b) Gao, Y.; Sharpless, K. B. J. Am. Chem. Soc. 1988, 110, 7538.
13. For a review on epoxides and halohydrins, see: Kasai, N.; Susuki, T.; Furukawa, Y. J. Mol. Catal. B 1998, 4, 237.
14. Leak, D. J.; Aikens, P. J.; Seyed-Mahmolldian, M. Tibtech 1992, 10, 256.
15. Harrisson, I. T.; Harrisson, S. Compendium of Organic Synthetic Methods; Wiley-Interscience: New York, 1971, 1974.
16. (a) Raja Rao, K. V.; Rao, L. J. M.; Prakasa Rao, N. S. Phytochemistry 1990, 29, 1326.
17. (b) Lontsi, D.; Sondengam, B. L.; Martin, M. T.; Bodo, B. Phytochemistry 1991, 30, 2361.
18. (c) Yeo, H.; Park, S. Y.; Kim, J. Phytochemistry 1998, 48, 1399.
19. (a) Rasmusson, G. H.; Reynolds, G. F., Steinberg, N. G.; Walton, E.; Patel, G. F.; Liang, T.; Cascieri, M. A.; Cheung, A. H.; Brooks, J. R.; Berman, C. J. Med. Chem. 1986, 29, 2298.
20. (b) Spera, G.; Lubrano, C. C. Int. J. Immunopathol. Pharmacol. 1996, 91, 33.
21. (c) Ling, Y. Z.; Li, J. S.; Kato, K.; Liu, Y.; Wang, X.; Klus, G. T.; Marat, K.; Nnane, I. P.; Brodie, A. M. H. Bioorg. Med. Chem. 1998, 6, 1683.
22. (a) Li, X.; Chen, C.; Singh, S. M.; Labire, F. Steroids 1995, 60, 430.
23. (b) Chen, W.; Zouboulis, C. C.; Orfanos, C. E. Dermatology 1996, 193, 177.
24. (a) García-Granados, A.; Dueñas, J.; Moliz, J. N.; Parra, A.; Pérez, F. L.; Dobado, J. A.; Molina, J. J. Chem. Res., Synop. 2000, 56; J. Chem. Res., Miniprint 2000, 326.
25. (b) García-Granados, A.; Dueñas, J.; Moliz, J. N.; Parra, A.; Pérez, F. L.; Dobado, J. A.; Molina, J. J. Chem. Res., Synop. 2000, 56; J. Chem. Res., Miniprint 2000, 326.
26. García-Granados, A.; Dueñas, J.; Melguizo, E.; Moliz, J. N.; Parra, A.; Pérez, F. L.; Dobado, J. A.; Molina, J. J. Chem. Res., Synop. 2000, 211; J. Chem. Res., Miniprint 2000, 653.
27. García-Granados, A.; Dueñas, J.; Melguizo, E.; Moliz, J. N.; Parra, A.; Pérez, F. L.; Dobado, J. A.; Molina, J. J. Chem. Res., Synop. 2000, 211; J. Chem. Res., Miniprint 2000, 653.
28. García-Granados, A.; Melguizo, E.; Parra, A.; Simeó, Y.; Viseras, B.; Dobado, J. A.; Molina, J.; Arias, J. M. J. Org. Chem. 2000, 65, 8214.
29. Monaco, P.; Caputo, R.; Palumbo, G.; Mangoni, L. Phytochemistry 1973, 12, 939.
30. Fortin, D.; Gaudette, F.; Marsault, E.; Deslongchamps, P. Tetrahedron 2001, 57, 4167.
31. Morzycki, J. W.; Wawer, I.; Gryszkiewicz, A.; Maj, J.; Siergiejczyk, L.; Zaworska, A. Steroids 2002, 67, 621.
32. Cremer, D.; Pople, J. A. J. Am. Chem. Soc. 1975, 97, 1354.
33. Gaussian 98, Revision A.7: M. J. Frisch, Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, J. A., Jr.; Stratmann, R. E.; Burant, J. C.; Dapprich, S.; Millam, J. M.; Daniels, A. D.; Kudin, K. N.; Strain, M. C.; Farkas, O.; Tomasi, J.; Barone, V.; Cossi, M.; Cammi, R.; Mennucci, B.; Pomelli, C.; Adamo, C.; Clifford, S.; Ochterski, J.; Petersson, G. A.; Ayala, P. Y.; Cui, Q.; Morokuma, K.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Cioslowski, J.; Ortiz, J. V.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Gonzalez, C.; Challacombe, M.; Gill, P. M. W.; Johnson, B. G.; Chen, W.; Wong, M. W.; Andres, J. L.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A.; Gaussian, Inc., Pittsburgh, PA, 1998.
34. (a) Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1998, 37, 785.
35. (b) Becke, A. D. J. Chem. Phys. 1993, 98, 5648.
36. Wolinski, K.; Hilton, J. F.; Pulay, P. J. Am. Chem. Soc. 1990, 112, 8251.
37. Haasnoot, C.; De-Leeuw, F.; Altona, C. Tetrahedron 1980, 36, 2783.
38. Farrugia, L. J. J. Appl. Crystallogr. 1997, 30, 565.
39. Sheldrick, G. M. SHELXTL-plus Reference Manual, Version 5.0; Bruker Analytical X-ray Systems: Madison, WI, 1996.