6-Chloro- and 6-bromo-substituted steroids in the Suzuki-Miyaura cross-coupling reaction. A convenient route to potential aromatase inhibitors

Synthesis

Volumn , Issue 3, 2006, Pages 533-539

  Lukashev, Nikolay V ^a   Latyshev, Gennadij V ^a   Donez, Pavel A ^a   Skryabin, George A ^b   Beletskaya, Irina P ^a  

^a MOSCOW STATE UNIVERSITY   (Russian Federation)

^b STE 1400   (United States)

Author keywords

Cross coupling; Nickel; Palladium; Steroids; Suzuki reaction

Indexed keywords

CATALYSTS; HYDROLYSIS; NICKEL; PALLADIUM; SUBSTITUTION REACTIONS;

CROSS-COUPLING; ENOL ETHERS; SUZUKI REACTION;

HORMONES;

6 BROMOSTEROID DERIVATIVE; 6 CHLOROSTEROID DERIVATIVE; AROMATASE INHIBITOR; CARBON; CHLORINE; DIOXANE; ENOL ETHER DERIVATIVE; ETHER DERIVATIVE; NICKEL; PALLADIUM; STEROID; TOLUENE; UNCLASSIFIED DRUG;

ARTICLE; ARYLATION; BREAST CANCER; CATALYST; CHEMICAL REACTION KINETICS; ENZYME INHIBITION; HYDROLYSIS; REACTION ANALYSIS; SUBSTITUTION REACTION; SUZUKI MIYAURA CROSS COUPLING REACTION; SUZUKI REACTION;

EID: 32644443585     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2006-926270     Document Type: Article

References (39)

1. Jemal, A.; Thomas, A.; Murray, T.; Thun, M. CA Cancer J. Clin. 2002, 52, 47.
2. Lake, D. E.; Hudis, C. Cancer Control 2002, 9, 490.
3. (a) Lonning, P. E. Eur. J. Cancer 2002, 38, S47.
4. (b) Choueiri, T. K.; Alemany, C. A.; Abou-Jawde, R. M.; Budd, G. T. Clin. Therapeutics 2004, 26, 1199.
5. (c) Rose, C. Am. J. Clin. Oncol. 2003, 26, S9.
6. (d) Buzdar, A. Endocrine-Related Cancer 1999, 6, 219.
7. (e) Sainsbury, R. Br. J. Cancer 2004, 90, 1733.
8. Levina, I. S. Russ. Chem. Rev. (Engl. Transl.) 1998, 67, 975.
9. (a) Numazawa, M.; Oshibe, M. J. Med. Chem. 1994, 37, 1312.
10. (b) Numazawa, M.; Oshibe, M.; Yamaguchi, S.; Tachibana, M. J. Med. Chem. 1996, 39, 1033.
11. (c) Numazawa, M.; Oshibe, M. Steroids 1995, 60, 506.
12. (d) Numazawa, M.; Yamaguchi, S. J. Steroid Biochem. Mol. Biol. 1998, 67, 41.
13. (e) Rao, P. N.; Acosta, C. K.; Bahr, M. L.; Burdett, J. E.; Cessac, J. W.; Morrison, P. A.; Kim, H. K. Steroids 2000, 65, 395.
14. (f) Rao, P. N.; Acosta, C. K.; Cessac, J. W.; Bahr, M. L.; Kim, H. K. Steroids 1999, 64, 205.
15. Skoda-Foldes, R.; Kollar, L. Chem. Rev. 2003, 103, 4095.
16. (a) Przezdziecka, A.; Kurek-Tyrlik, A.; Wicha, J. Collect. Czech. Chem. Commun. 2002, 67, 1658.
17. (b) Arcadi, A.; Burini, A.; Cacchi, S.; Delmastro, M.; Marinelli, F.; Pietroni, B. Synlett 1990, 47.
18. (c) Potter, G. A.; Barrie, S. E.; Jarman, M.; Rowlands, M. G. J. Med. Chem. 1995, 38, 2463.
19. (d) Ciattini, P. G.; Morera, E.; Ortar, G. Tetrahedron Lett. 1990, 31, 1889.
20. (a) Gravett, E. C.; Hilton, J. P.; Jones, K.; Romero, F. Tetrahedron Lett. 2001, 42, 9081.
21. (b) Ciattini, P. G.; Morera, E.; Ortar, G. Tetrahedron Lett. 1992, 33, 4815.
22. Lukashev, N. V.; Latyshev, G. V.; Donez, P. A.; Skryabin, G. A.; Beletskaya, I. P. Synthesis 2005, 1578.
23. (a) Hesse, S.; Kirsch, G. Synthesis 2001, 755.
24. (b) Satoh, N.; Ishiyama, T.; Miyaura, N.; Suzuki, A. Bull. Chem. Soc. Jpn. 1987, 60, 3471.
25. (a) Indolese, A. F. Tetrahedron Lett. 1997, 38, 3513.
26. (b) Hassan, J.; Sevignon, M.; Gozzi, C.; Schulz, E.; Lemaire, M. Chem. Rev. 2002, 102, 1359.
27. (c) Beletskaya, I. P.; Tsvetkov, A. V.; Latyshev, G. V.; Lukashev, N. V. Russ. J. Org. Chem. (Eng. Transl.) 2003, 39, 1660.
28. (a) Beletskaya, I. P.; Cheprakov, A. V. In Handbook of Organopalladium Chemistry, Vol. 2; Negishi, E. I., Ed.; Wiley Interscience: New York, 2002, 2957-3006.
29. (b) Beletskaya, I. P.; Cheprakov, A. V. J. Organomet. Chem. 2004, 689, 4055.
30. Littke, A. F.; Dai, C.; Fu, G. C. J. Am. Chem. Soc. 2000, 122, 4020.
31. Li, G. Y. J. Org. Chem. 2002, 67, 3643.
32. (a) Jones, D.; Knox, K. J. Chem. Soc., Chem. Commun. 1975, 165.
33. (b) Collins, D.; Jackson, R.; Timms, R. Tetrahedron Lett. 1976, 495.
34. (c) McQuillin, F. J. Chem. Soc., Chem. Commun. 1978, 15.
35. (d) Butters, T.; Handschuh, D.; Hutter, P.; Winter, W. Liebigs Ann. Chem. 1982, 1111.
36. (e) Hunt, D.; Quante, J.; Tyson, R.; Dashev, L. J. Org. Chem. 1984, 49, 5262.
37. (f) Trost, B.; Verhoeven, T. J. Am. Chem. Soc. 1978, 100, 3435.
38. Sperandio, A.; Tuozzi, A.; Bocelli, G.; Sterzo, C. L. Tetrahedron 1999, 55, 461.
39. Kashirskoe shosse 9, b. 3, Moscow, 115230, Russia. Tel/ Fax:+7(095)7778495.