y-Lactones Upon Double Nucleophilic Additions of Bis(tms)Ketene Acetals to P-Systems and Access to New-Towards Cancer Cells Cytotoxic-Endoperoxide Lactones
DOI:
https://doi.org/10.29356/jmcs.v52i2.1062Keywords:
endoperoxide lactones, cytotoxic activities, y-lactones, bis(TMS)ketene acetals, tricarbonylchromium complexes, double nucleophilic additionsAbstract
Arenechromium and cycloheptatrienechromium complexes react with (TMS)ketene acetals to give upon a double nucleophilic addition either diene-lactones or cyclohexenone-lactones. 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.
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References
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71. Clennan, E. L.; Pace, A. Tetrahedron 2005, 61, 6665-6691.
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73. Pearson, A. J.; Srinivasan, K. J. Org. Chem. 1992, 67, 3965-3973.
74. Monks, A.; Scudiero, D.; Skehan, P.; Shoemaker, R.; Paull, K.; Vistica, D.; Hose, C.; Langley, J.; Cronise, P.; Vaigro-Wolff, A.; Gray-Goodrich, M.; Campbell, H.; Mayo, J.; Boyd. M. Journal of the National Cancer Institute 1991, 83, 11, 757-766.
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2. Cornils, B.; Hermann, W. A. in: Applied Homogeneous Chemistry with Organometallic Compounds, Vol 1, VCH, Ed. Weinheim 1996, 554.
3. Collins, A. N.; Sheldrake, G. N. in: Chirality in Industry, Crosby, J., Ed., Wiley, J., N.Y. 1992, 303.
4. Culkin, D. A.; Hartwig, J. F. Acc. Chem. Res. 2003, 36, 234-245.
5. Liu, X.; Hartwig, J. F. J. Am. Chem. Soc. 2004, 126, 5182-5191.
6. Moradi, W. A.; Buchwald, S. L. J. Am. Chem. Soc. 2001, 123, 7996-8002.
7. Card, R. J.; Trahanovsky, W. S. Tetrahedron Lett. 1973, 3823-3824.
8. Card, R.; Trahanovsky, W. J. Org. Chem. 1980, 45, 2560-2566.
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10. Semmelhack, M. F.; Hall, H. T.; Yoshifuji, M. J. Am. Chem. Soc. 1976, 98, 6387-6389.
11. Semmelhack, M. F.; Clark, G. J. Am. Chem. Soc. 1977, 99, 1675-1676.
12. Semmelhack, M. F.; Clark, G.; Farina, R.; Saeman, M. J. Am. Chem. Soc. 1979, 101, 217-218.
13. Semmelhack, M. F.; Clark, G.; Garcia, J. L.; Harrison, J. J.; Thebtaranonth, Y.; Wulff W.; Yamashita, A. Tetrahedron 1981, 37, 3957-3965.
14. Kündig, E. P. Pure Appl. Chem. 1985, 57, 1855-1864.
15. Pape, A. R.; Kaliappan, K. P.; Kündig, E. P. Chem. Rev. 2000, 100, 2917-2940.
16. Bellassoued, M.; Chelain, E.; Collot, J.; Rudler, H.; Vaissermann, J. J. Chem. Soc. Chem. Commun. 1999, 187-188.
17. Rudler, H.; Comte, V.; Bellassoued, M.; Garrier, E.; Vaissermann, J.; Daran, J. C. C. R. Acad. Sci. Paris, Série IIc 2000, 113-122.
18. Rudler, H.; Comte, V.; Garrier, E.; Bellassoued, M.; Chelain, E.; Vaissermann, J. J. Organomet. Chem. 2001, 621, 284-298.
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 1991,182-231.
20. Rudler, H.; Alvarez, C.; Parlier, A.; Aldeco-Pérez, E.; Denise, B.; Xu, Y.; Vaissermann, J. Tetrahedron Lett. 2004, 45, 2409-2411.
21. Rudler, H.; Denise, B.; Parlier, A.; Daran, J. C. Chem. Commun. 2002, 940-941.
22. Rudler, H.; Denise, B.; Xu, Y.; Parlier, A.; Vaissermann J. Eur. J. Org. Chem. 2005, 3724-3749.
23. Rudler, H.; Denise, B.; Xu, Y.; Vaissermann J. Tetrahedron Lett. 2005, 46, 3449-3451.
24. Klayman, D. L. Science 1985, 228, 1049-1055.
25. Posner, G. H.; Wang, D.; González, L.; Tao, X. Tetrahedron Lett. 1996, 37, 815-818.
26. Zhou, W. S. Pure Appl. Chem. 1986, 58, 817-824.
27. Robert, A.; Meunier, B. Chem. Soc. Rev. 1998, 27, 273-279.28. Posner, G.; O’Neill, P. M. Acc. Chem. Res. 2004, 37, 397-404.
29. Wang, D-Y.; Wu, Y-L.; Wu, Y.; Li, Y. J. Chem. Soc. Perkin Trans.1 2001, 605-609.
30 Grellepois, F.; Chorki, F.; Crousse, B.; Ourévitch, M.; Bonnet-Delpon, D.; Bégué, J. P. J. Org. Chem. 2002, 67, 1253-1260.
31. Chen, Y.; McCarthy, P. J.; Harmody, D. K.; Schimoler-O’Rourke, R.; Chilson, K.; Selitrennikoff, C.; Pomponi, S. H.; Wright, A. E. J. Nat. Prod. 2002, 65, 1509-1512.
32. El Sayed, K. A.; Hamann, M. T.; Hashish, N. A.; Shier, W. T.; Kelly, M.; Khan, A. A. J. Nat. Prod. 2001, 64, 522-524.
33. Kashman, Y.; Rotem, M. Tetrahedron Lett. 1979, 19, 1707-1709.
34. Albericci, A.; Braekman, J. C.; Daloze, D.; Tursch, B. Tetrahedron 1982, 38, 1881-1890.
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,
1483-1487.
36 Aldeco-Pérez, E.; Rudler, H.; Parlier, A.; Alvarez, C.; Apan, M. T.; Herson, P.; Toscano, A. Tetrahedron Lett. 2006, 47, 9053-9056.
37. For the hydrolysis of cyclic dienol ethers see Pearson, A. J.; Gontcharov, A.V. J. Org. Chem. 1998, 63, 152-162.
38. Colton, F. B.; Nysted, L. N.; Riegel, B.; Raymond, L. A. J. Am. Chem. Soc. 1957, 79, 1123-1127.
39. Hartman, J.; Tomasewski, A. J.; Dreiding, A. S. J. Am. Chem. Soc. 1956, 78, 5662-5666.
40. Gevorgyan, V.; Yamamoto, Y. J. Chem. Soc., Chem. Commun. 1994, 59-60.
41. Jung, M. E.; Lyster, M. A. J. Org. Chem. 1977, 42, 3761-3764.
42. Olah, G. A.; Narang, S. C.; Gupta, B. G. B.; Malhotra, R. J. Org. Chem. 1979, 44, 1247-1251.
43. Semmelhack, M.; Hall, H. T.; Farina, R.; Yoshifuji, M.; Clark, G.; Bargar, T.; Hirotsu, K.; Clardy, J. J. Am. Chem. Soc. 1979, 101, 3535-3544.
44. Falck, J. R.; Barma, D. K.; Baati, R.; Mioskowski, C. Angew. Chem.Int.Ed. 2001, 40, 1281-1283.
45. The calculations were performed using the B3LYP function and the Dunning aug-cc-pvdz basis set with the GAUSSIAN03 code.
46. Gaussian 03, Revision C.02, Frisch, M. J. Gaussian Inc., Wallingford CT 2004.
47. Hansch, C.; Leo, A.; Taft, R.W. Chem. Rev. 1991, 91, 165-195.
48. Xu, Y.; Aldeco-Perez, E.; Rudler, H.; Parlier, A.; Denise, B.; Álvarez, C. Tetrahedron Lett. 2006, 47, 4553-4556.
49. Müller, P. M.; Pfister, P. M. Helv. Chim. Acta 1983, 66, 771-779.
50. Lansbury, P. T.; Hangauer, D. G.; Vacca, J. P. J. Am. Chem. Soc. 1980, 102, 3964-3965.
51. Sato, Y.; Oketani, H.; Yamada, T. J. Pharm. Pharmacol 1997, 49, 1042-1044.
52. Bruno, M.; Roselli, S.; Maggio, A.; Raccuglia, R. A.; Bastow, K. F.; Lee K. H. J. Nat. Prod. 2005, 68, 1042-1046.
53. Srikrishna, A.; Dethe, D. H. Org. Lett. 2004, 6, 165-168.
54. Higuchi, Y.; Shimoma, F.; Ando, M. J. Nat. Prod. 2003, 66, 810-817.
55. Nosse, B.; Chhor, R. B.; Jeong, W. B.; Böhm, C.; Reiser, O. Org. Lett. 2003, 5, 941-945.
56. Pearson, A. J.; Khan, M. N. I. J. Org. Chem. 1985, 50, 5276-5285.
57. Pearson, A. J.; Bruhn, P.; Richards, I. C. Tetrahedron Lett. 1984, 25, 387-390.
58. Pearson, A. J. Synlett 1990, 10-19.
59. Abel, E. W.; Bennett, M. A.; Burton, R.; Wilkinson, G. J. Chem. Soc. 1958, 4559-4563.
60. Sato, Y.; Oketani, H.; Yamada, T.; Singyouchi, K.; Ohtsubo, T.; Kihara, M.; Shibata, H.; Higuti, T. J. Pharm. Pharmacology 1997, 49, 1042-1044.
61. Pauson, P. L.; Smith, G. H.; Valentine, J. H. J. Chem. Soc. C, 1967, 1061-1065.
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, 107-113.
64. Ranganathan, S.; Muraleedharan, K. M.; Vaish, N. K.; Jayaramam, N. Tetrahedron 2004, 60, 5273-5308.
65. Yeh, M. C. P.; Chuang, C. N. J. Chem. Soc., Chem. Commun. 1994, 703-704.
66. Chen, W.; Sheridan, J. B.; Coté, M. L.; Lalancette, R. A. Organometallics 1996, 15, 2700-2706.
67. Beckwith, R. E. J.; Gravestock, M. B.; Simpkins, N. S. J. Chem. Soc. Perkin Trans. 1 2002, 2352-2359.
68. For a discussion on the regioselectivity of nucleophile additions to polyene complexes see Sautet, P.; Eisenstein, O.; Nicholas, K. M. Organometallics 1987, 6, 1845-1849.
69. Carruthers, W. Cycloaddition Reactions in Organic Synthesis. Pergamon Press, New-York, 1990.
70. For spontaneous Diels-Alder reactions see for example, Li, C.; Johnson, R. P.; Porco, Jr., J. A. J. Am. Chem. Soc. 2003, 125, 5095-5106.
71. Clennan, E. L.; Pace, A. Tetrahedron 2005, 61, 6665-6691.
72. Bernardinelli, G.; Jefford, C. W.; Richardson, G. D.; Dossier., J. C. Acta Crystallogr. 1991, C47, 388-392.
73. Pearson, A. J.; Srinivasan, K. J. Org. Chem. 1992, 67, 3965-3973.
74. Monks, A.; Scudiero, D.; Skehan, P.; Shoemaker, R.; Paull, K.; Vistica, D.; Hose, C.; Langley, J.; Cronise, P.; Vaigro-Wolff, A.; Gray-Goodrich, M.; Campbell, H.; Mayo, J.; Boyd. M. Journal of the National Cancer Institute 1991, 83, 11, 757-766.
75. Ainsworth, C.; Kuo,Y. N. J. Organomet. Chem. 1972, 46, 73-87.
76. Brady, W.; Agho, M. O. J. Heterocycl. Chem. 1983, 20, 501-506.
77. Bellassoued, M.; Ennigrou, R.; Gaudemar, M. J. Organomet. Chem. 1988, 338, 149-158.
78. Bellassoued, M.; Ennigrou, R.; Gaudemar, M. J. Organomet. Chem. 1990, 393, 19-25.
79. Herrmann, J. L.; Kieczykowski, G. R.; Schlessinger, R. H. Tetrahedron Lett. 1973, 2433-2436.
80. Effenberger, F.; Schöllkopf, K. Chem. Ber. 1985, 118, 4356-4376.
81. Guzei, I. A.; Czerwinski, C. J. Acta Crystallogr. 2004, C60, M615-M617.
82. Kolehmainen, E.; Laihia, K.; Korvola, J.; Kaganovich, V. S.; Rybinskaya, M. I.; Kerzina, Z. A. J. Organomet. Chem. 1995, 487, 215-221.
83. Davies, S. G.; Goodfellow, C. L. J. Chem. Soc., Perkin Trans. 1 1990, 393-407.
84. Djukic, J. P. ; Maisse, A. ; Pfeffer, M. J. Organomet. Chem. 1998, 567, 65-74.
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 CB21 EZ, UK (fax 1223-336033 or e-mail [email protected]).
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