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Journal of the Mexican Chemical Society
versão impressa ISSN 1870-249X
J. Mex. Chem. Soc vol.52 no.2 Ciudad de México Abr./Jun. 2008
Article
γLactones Upon Double Nucleophilic Additions of Bis(TMS)Ketene Acetals to Πsystems and Access to Newtowards Cancer Cells CytotoxicEndoperoxide Lactones
Henri Rudler,1* Eugenia AldecoPérez,2 Andrée Parlier,1 Cecilio Álvarez,2 Patrick Chaquin,1 Patrick Herson,1 Alfredo Toscano,2 and MaríaTeresa RamírezApan2
1 Université Pierre et Marie Curie, Laboratoire de Chimie Organique, UMR 7611CNRS, Institut de Chimie Moléculaire FR 2769, 4 place Jussieu, CC 47, 75252 Paris Cedex 5, France.
2 Instituto de Química, Universidad Nacional Autónoma de México, Circuito Exterior, Ciudad Universitaria, Coyoacán 04510, México D.F., México. *Responsible author: rudler@ccr.jussieu.fr.
Recibido el 16 de noviembre de 2007
Aceptado el 20 de mayo de 2008
Abstract
Arenechromium and cycloheptatrienechromium complexes react with (TMS)ketene acetals to give upon a double nucleophilic addition either dienelactones or cyclohexenonelactones. In the first case, the scope of the reaction and the stability of the dienes were examined: they could be easily transformed either in arylpropionic acids or in conjugated ketones and more interestingly, they reacted with oxygen to give new highly active cytotoxic endoperoxide lactones. Unfortunately, in the second case, no further functionalization could be achieved up to now.
Key words: Endoperoxide lactones, cytotoxic activities, γlactones, feis(TMS)ketene acetals, tricarbonylchromium complexes, double nucleophilic additions.
Resumen
Se describe la reacción entre complejos arentricarbonilcromo y cicloheptatrientricarbonilcromo con acetales de bis(trimetil silil)cetena, la cual mediante una doble adición nucleofílica conduce a la formación tanto de dienolactonas como ciclohexenonalactonas. En el primer caso, se examinó la estabilidad de los dienos: pudiendo éstos transformarse fácilmente en ácidos arilpropiónicos o en cetonas conjugadas y al reaccionar con oxígeno en nuevas endoperoxolactonas con actividad citotóxica importante. Desafortunadamente, en el segundo caso, no pudo realizarse la funcionalización posterior de dichas moléculas.
Palabras clave: Endoperoxolactonas, actividad citotóxica, γlactonas, acetales de bis(trimetilsilil)cetena, complejos de tricarbonilcromo, doble adición nucleofílica.
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References
1. Adams, S. S. Chemistry in britain 1987, 23, 11931195. [ Links ]
2. Cornils, B.; Hermann, W. A. in: Applied Homogeneous Chemistry with Organometallic Compounds, Vol 1, VCH, Ed. Weinheim 1996, 554. [ Links ]
3. Collins, A. N.; Sheldrake, G. N. in: Chirality in Industry, Crosby, J., Ed., Wiley, J., N.Y. 1992, 303. [ Links ]
4. Culkin, D. A.; Hartwig, J. F. Acc. Chem. Res. 2003, 36, 234245. [ Links ]
5. Liu, X.; Hartwig, J. F. J. Am. Chem. Soc. 2004, 126, 51825191. [ Links ]
6. Moradi, W. A.; Buchwald, S. L. J. Am. Chem. Soc. 2001, 123, 79968002. [ Links ]
7. Card, R. J.; Trahanovsky, W. S. Tetrahedron Lett. 1973, 38233824. [ Links ]
8. Card, R.; Trahanovsky, W. J. Org. Chem. 1980, 45, 25602566. [ Links ]
9. Semmelhack, M. F. in: Comprehensive Organometallic Chemistry II, Vol.12, Abel, E. W.; Stone, F. G. A.; Wilkinson, G. Eds., Pergamon, Oxford, U.K. 1995, 9791015. [ Links ]
10. Semmelhack, M. F.; Hall, H. T.; Yoshifuji, M. J. Am. Chem. Soc. 1976, 98, 63876389. [ Links ]
11. Semmelhack, M. F.; Clark, G. J. Am. Chem. Soc. 1977, 99, 16751676. [ Links ]
12. Semmelhack, M. F.; Clark, G.; Farina, R.; Saeman, M. J. Am. Chem. Soc. 1979, 101, 217218. [ Links ]
13. Semmelhack, M. F.; Clark, G.; Garcia, J. L.; Harrison, J. J.; Thebtaranonth, Y.; Wulff W.; Yamashita, A. Tetrahedron 1981, 37, 39573965. [ Links ]
14. Kündig, E. P. Pure Appl. Chem. 1985, 57, 18551864. [ Links ]
15. Pape, A. R.; Kaliappan, K. P.; Kündig, E. P. Chem. Rev. 2000, 100, 29172940. [ Links ]
16. Bellassoued, M.; Chelain, E.; Collot, J.; Rudler, H.; Vaissermann, J. J. Chem. Soc. Chem. Commun. 1999, 187188. [ Links ]
17. Rudler, H.; Comte, V.; Bellassoued, M.; Garrier, E.; Vaissermann, J.; Daran, J. C. C. R. Acad. Sci. Paris, Série IIc 2000, 113122. [ Links ]
18. Rudler, H.; Comte, V.; Garrier, E.; Bellassoued, M.; Chelain, E.; Vaissermann, J. J. Organomet. Chem. 2001 , 621, 284298. [ Links ]
19. For examples of sequential addition reactions see, McQuillin, F. J.; Parker, D. G.; Stephenson, G. R. in: Transition Metal Organometallics for Organic Synthesis; Cambridge University Press: Cambridge, UK 1991,182231. [ Links ]
20. Rudler, H.; Alvarez, C.; Parlier, A.; AldecoPérez, E.; Denise, B.; Xu, Y.; Vaissermann, J. Tetrahedron Lett. 2004, 45, 24092411. [ Links ]
21. Rudler, H.; Denise, B.; Parlier, A.; Daran, J. C. Chem. Commun. 2002, 940941. [ Links ]
22. Rudler, H.; Denise, B.; Xu, Y.; Parlier, A.; Vaissermann J. Eur. J. Org. Chem. 2005, 37243749. [ Links ]
23. Rudler, H.; Denise, B.; Xu, Y.; Vaissermann J. Tetrahedron Lett. 2005, 46, 34493451. [ Links ]
24. Klayman, D. L. Science 1985, 228, 10491055. [ Links ]
25. Posner, G. H.; Wang, D.; González, L.; Tao, X. Tetrahedron Lett. 1996, 37, 815818. [ Links ]
26. Zhou, W. S. Pure Appl. Chem. 1986, 58, 817824. [ Links ]
27. Robert, A.; Meunier, B. Chem. Soc. Rev. 1998, 27, 273279. [ Links ]
28. Posner, G.; O'Neill, P. M. Acc. Chem. Res. 2004, 37, 397404. [ Links ]
29. Wang, DY.; Wu, YL.; Wu, Y.; Li, Y. J. Chem. Soc. Perkin Trans.1 2001, 605609. [ Links ]
30 Grellepois, F.; Chorki, F.; Crousse, B.; Ourévitch, M.; BonnetDelpon, D.; Bégué, J. P. J. Org. Chem. 2002, 67, 12531260. [ Links ]
31. Chen, Y.; McCarthy, P. J.; Harmody, D. K.; SchimolerO'Rourke, R.; Chilson, K.; Selitrennikoff, C.; Pomponi, S. H.; Wright, A. E. J. Nat. Prod. 2002, 65, 15091512. [ Links ]
32. El Sayed, K. A.; Hamann, M. T.; Hashish, N. A.; Shier, W. T.; Kelly, M.; Khan, A. A. J. Nat. Prod. 2001, 64, 522524. [ Links ]
33. Kashman, Y.; Rotem, M. Tetrahedron Lett. 1979, 19, 17071709. [ Links ]
34. Albericci, A.; Braekman, J. C.; Daloze, D.; Tursch, B. Tetrahedron 1982, 38, 18811890. [ Links ]
35. Perry, T. L.; Dickerson, A.; Khan, A. A.; Kondru, R. K.; Beratan, D. N.; Wipf, P.; Kelly, M.; Hamann, M. T. Tetrahedron 2001, 57, 14831487. [ Links ]
36 AldecoPérez, E.; Rudler, H.; Parlier, A.; Alvarez, C.; Apan, M. T.; Herson, P.; Toscano, A. Tetrahedron Lett. 2006, 47, 90539056. [ Links ]
37. For the hydrolysis of cyclic dienol ethers see Pearson, A. J.; Gontcharov, A.V. J. Org. Chem. 1998, 63, 152162. [ Links ]
38. Colton, F. B.; Nysted, L. N.; Riegel, B.; Raymond, L. A. J. Am. Chem. Soc. 1957, 79, 11231127. [ Links ]
39. Hartman, J.; Tomasewski, A. J.; Dreiding, A. S. J. Am. Chem. Soc. 1956, 78, 56625666. [ Links ]
40. Gevorgyan, V.; Yamamoto, Y. J. Chem. Soc., Chem. Commun. 1994, 5960. [ Links ]
41. Jung, M. E.; Lyster, M. A. J. Org. Chem. 1977, 42, 37613764. [ Links ]
42. Olah, G. A.; Narang, S. C.; Gupta, B. G. B.; Malhotra, R. J. Org. Chem. 1979, 44, 12471251. [ Links ]
43. Semmelhack, M.; Hall, H. T.; Farina, R.; Yoshifuji, M.; Clark, G.; Bargar, T.; Hirotsu, K.; Clardy, J. J. Am. Chem. Soc. 1979, 101, 35353544. [ Links ]
44. Falck, J. R.; Barma, D. K.; Baati, R.; Mioskowski, C. Angew. Chem. Int. Ed. 2001, 40, 12811283. [ Links ]
45. The calculations were performed using the B3LYP function and the Dunning augccpvdz basis set with the GAUSSIAN03 code.
46. Gaussian 03, Revision C.02, Frisch, M. J. Gaussian Inc., Wallingford CT 2004. [ Links ]
47. Hansch, C.; Leo, A.; Taft, R.W. Chem. Rev. 1991, 91, 165195. [ Links ]
48. Xu, Y.; AldecoPerez, E.; Rudler, H.; Parlier, A.; Denise, B.; Álvarez, C. Tetrahedron Lett. 2006, 47, 45534556. [ Links ]
49. Müller, P. M.; Pfister, P. M. Helv. Chim. Acta 1983, 66, 771779. [ Links ]
50. Lansbury, P. T.; Hangauer, D. G.; Vacca, J. P. J. Am. Chem. Soc. 1980, 102, 39643965. [ Links ]
51. Sato, Y.; Oketani, H.; Yamada, T. J. Pharm. Pharmacol 1997, 49, 10421044. [ Links ]
52. Bruno, M.; Roselli, S.; Maggio, A.; Raccuglia, R. A.; Bastow, K. F.; Lee K. H. J. Nat. Prod. 2005, 68, 10421046. [ Links ]
53. Srikrishna, A.; Dethe, D. H. Org. Lett. 2004, 6, 165168. [ Links ]
54. Higuchi, Y.; Shimoma, F.; Ando, M. J. Nat. Prod. 2003, 66, 810817. [ Links ]
55. Nosse, B.; Chhor, R. B.; Jeong, W. B.; Bohm, C.; Reiser, O. Org. Lett. 2003, 5, 941945. [ Links ]
56. Pearson, A. J.; Khan, M. N. I. J. Org. Chem. 1985, 50, 52765285. [ Links ]
57. Pearson, A. J.; Bruhn, P.; Richards, I. C. Tetrahedron Lett. 1984, 25, 387390. [ Links ]
58. Pearson, A. J. Synlett 1990, 1019. [ Links ]
59. Abel, E. W.; Bennett, M. A.; Burton, R.; Wilkinson, G. J. Chem. Soc. 1958, 45594563. [ Links ]
60. Sato, Y.; Oketani, H.; Yamada, T.; Singyouchi, K.; Ohtsubo, T.; Kihara, M.; Shibata, H.; Higuti, T. J. Pharm. Pharmacology 1997, 49, 10421044. [ Links ]
61. Pauson, P. L.; Smith, G. H.; Valentine, J. H. J. Chem. Soc. C, 1967, 10611065. [ Links ]
62. Similar results were obtained from enolates originating from the corresponding esters and LDA (see the experimental section).
63. Hadley, F. J.; Gilbert, T. M.; Rogers, R. D. J. Organomet. Chem. 1993, 455, 107113. [ Links ]
64. Ranganathan, S.; Muraleedharan, K. M.; Vaish, N. K.; Jayaramam, N. Tetrahedron 2004, 60, 52735308. [ Links ]
65. Yeh, M. C. P.; Chuang, C. N. J. Chem. Soc., Chem. Commun. 1994, 703704. [ Links ]
66. Chen, W.; Sheridan, J. B.; Coté, M. L.; Lalancette, R. A. Organometallics 1996, 15, 27002706. [ Links ]
67. Beckwith, R. E. J.; Gravestock, M. B.; Simpkins, N. S. J. Chem. Soc. Perkin Trans. 1 2002, 23522359. [ Links ]
68. For a discussion on the regioselectivity of nucleophile additions to polyene complexes see Sautet, P.; Eisenstein, O.; Nicholas, K. M. Organometallics 1987, 6, 18451849. [ Links ]
69. Carruthers, W. Cycloaddition Reactions in Organic Synthesis. Pergamon Press, NewYork, 1990. [ Links ]
70. For spontaneous DielsAlder reactions see for example, Li, C.; Johnson, R. P.; Porco, Jr., J. A. J. Am. Chem. Soc. 2003, 125, 50955106. [ Links ]
71. Clennan, E. L.; Pace, A. Tetrahedron 2005, 61, 66656691. [ Links ]
72. Bernardinelli, G.; Jefford, C. W.; Richardson, G. D.; Dossier., J. C. Acta Crystallogr. 1991, C47, 388392. [ Links ]
73. Pearson, A. J.; Srinivasan, K. J. Org. Chem. 1992, 67, 39653973. [ Links ]
74. Monks, A.; Scudiero, D.; Skehan, P.; Shoemaker, R.; Paull, K.; Vistica, D.; Hose, C.; Langley, J.; Cronise, P.; VaigroWolff, A.; GrayGoodrich, M.; Campbell, H.; Mayo, J.; Boyd. M Journal of the National Cancer Institute 1991 , 83, 11, 757766. [ Links ]
75. Ainsworth, C.; Kuo,Y. N. J. Organomet. Chem. 1972, 46, 7387. [ Links ]
76. Brady, W.; Agho, M. O. J. Heterocycl. Chem. 1983, 20, 501506. [ Links ]
77. Bellassoued, M.; Ennigrou, R.; Gaudemar, M. J. Organomet. Chem. 1988, 338, 149158. [ Links ]
78. Bellassoued, M.; Ennigrou, R.; Gaudemar, M. J. Organomet. Chem. 1990, 393, 1925. [ Links ]
79. Herrmann, J. L.; Kieczykowski, G. R.; Schlessinger, R. H. Tetrahedron Lett. 1973, 24332436. [ Links ]
80. Effenberger, F.; Schollkopf, K. Chem. Ber. 1985, 118, 43564376. [ Links ]
81. Guzei, I. A.; Czerwinski, C. J. Acta Crystallogr. 2004, C60, M615M617. [ Links ]
82. Kolehmainen, E.; Laihia, K.; Korvola, J.; Kaganovich, V. S.; Rybinskaya, M. I.; Kerzina, Z. A. J. Organomet. Chem. 1995, 487, 215221. [ Links ]
83. Davies, S. G.; Goodfellow, C. L. J. Chem. Soc., Perkin Trans. 1 1990, 393407. [ Links ]
84. Djukic, J. P. ; Maisse, A. ; Pfeffer, M. J. Organomet. Chem. 1998, 567, 6574. [ Links ]
85. Crystallographic data for 26b, 27, 32b, 33b, 34d, 39a, 41a, have been deposited with the Cambridge Data Center as supplementary material, publication numbers CCDC 278719, CCDC 278520, CCDC 221173, CCDC 663972, CCDC 221174, CCDC 607822, CCDC 278208 respectively. Copies of the data can be obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge CB2 1 EZ, UK (fax 1223336033 or email deposit@ccdc.cam.ac.uk). [ Links ]