A convenient enantioselective synthesis of 3-asymmetrically substituted oxindoles as progesterone receptor antagonists

Tetrahedron Letters

Volumn 52, Issue 30, 2011, Pages 3945-3948

  Alluri, S ^a   Feng, H ^a   Livings, M ^a   Samp, L ^a   Biswas, D ^a   Lam, T W ^b   Lobkovsky, E ^c   Ganguly, A K ^a  

^a Stevens Institute of Technology   (United States)

^b MERCK RESEARCH LABORATORIES   (United States)

^c Department of Obstetrics Gynecology   (United States)

Author keywords

Desulfurisation; Enantioselective synthesis; Progesterone receptor antagonist; Radical cyclization

Indexed keywords

2 PROPANOL; ANTIGESTAGEN; NICKEL; OXINDOLE; PHENETHYL ALCOHOL;

ARTICLE; CHEMICAL MODIFICATION; DIASTEREOISOMER; DRUG SYNTHESIS; ENANTIOMER; ENANTIOSELECTIVITY; IC 50; RACEMIC MIXTURE; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

EID: 79959522577     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2011.05.120     Document Type: Article

References (25)

1. A.K. Ganguly, C.H. Wang, T.M. Chan, Y.H. Ing, and A.V. Buevich Tetrahedron Lett. 45 2004 883
2. X.Z. Wearing, and J.M. Cook Org. Lett. 4 2002 4237
3. B.K. Albrecht, and R.M. Williams Org. Lett. 5 2003 197
4. S.E. Reisman, J.M. Ready, M.M. Weiss, A. Hasuoka, M. Hirata, K. Tamaki, T.V. Ovaska, C.J. Smith, and J.L. Wood J. Am. Chem. Soc. 130 2008 2087
5. A.H. Abadi, S.M. Abou-Seri, D.E. Abdel-Rahman, C. Klein, O. Lozach, and L. Meijer Eur. J. Med. Chem. 41 2006 296
6. For enantioselective synthesis, see: X. Tian, K. Jiang, J. Peng, W. Du, and Y.-C. Chen Org. Lett. 10 2008 3583
7. Y. Yasui, H. Kamisaki, and Y. Takemoto Org. Lett. 10 2008 3303
8. B.M. Trost, and Y. Zhang J. Am. Chem. Soc. 129 2007 14548
9. E.C. Linton, and M.C. Kozlowski J. Am. Chem. Soc. 130 2008 16162
10. X.-H. Chen, Q. Wei, S.-W. Luo, H. Xiao, and L.-Z. Gong J. Am. Chem. Soc. 131 2009 13819
11. NMR and high resolution mass spectra of all the compounds described in this Letter were consistent with the assigned structures. Assignments were further confirmed using 2D NMR and NOE experiments. It should be noted that the yields (represented as Y) reported in this Letter are not optimised. The purity of the compounds was established using various chromatographic techniques. Compounds (3-9), (11), (12), (15), (18-20), (23), (27), (30), and (31) were not crystalline. All other compounds described in the paper were crystalline. Crystals were obtained from DCM-hexane for compounds (1), (2), (21), (22), (25), (26), (28), (29), and (32). The melting points of compounds (1), (2), (21), (22), (25), (26), (28), (29), (32) were 88-90, 96-97, 118-120, 81-82, 95-97, 130-132, 117-118, 96-97, 103-104 °C, respectively.
12. A. Fensome, W.R. Adams, A.L. Adams, T.J. Berrodin, J. Cohen, C. Huselton, A. Illenberger, J.C. Kern, V.A. Hudak, M.A. Marella, E.G. Melenski, C.C. McComas, C.A. Mugford, O.D. Slayden, M. Yudt, Z. Zhang, P. Zhang, Y. Zhu, R.C. Winneker, and J.E. Wrobel J. Med. Chem. 51 2008 1861
13. A. Fensome, R. Bender, J. Cohen, M.A. Collins, V.A. Mackener, L.L. Miller, J.W. Ullrich, R. Winneker, J. Wrobel, P. Zhang, Z. Zhang, and Y. Zhu Bioorg. Med. Chem. Lett. 12 2002 3487
14. R.N. Brogden, K.L. Goa, and D. Faulds Drugs 45 1993 384
15. K. Chwalisz, D. DeManno, R. Garg, L. Larsen, C. Mattia-Goldberg, and T. Stickler Semin. Reprod. Med. 22 2004 113
16. K. Chwalisz, L. Larsen, C. Mattia-Goldberg, A. Edmonds, W. Elger, and A. Winkel Craig Fertil. Steril. 87 2007 1399
17. L. Fedele, and N. Berlanda Exp. Opin. Emerging Drugs 9 2004 167
18. L.M. Kettel, A.A. Murphy, A.J. Morales, and S.S.C. Yen Am. J. Obstet. Gynecol. 178 1998 1151
19. L.M. Kettel Int. Congr., Symp. Semin. Ser. 13 1997 334 (Endometriosis Today)
20. R.S. Baker, A.F. Parsons, and M. Wilson Tetrahedron Lett. 39 1998 331
21. 1H NMR (400 MHz): δ ppm 7.94 (d, 1H, J = 7.4 Hz), 7.38-7.24 (m, 6H), 7.10 (t, 1H, J = 7.5 Hz), 6.85 (d, 1H, J = 7.8 Hz), 5.32 (d, 1H, J = 5.3 Hz), 4.78 (q, 1H, J = 6.4 Hz), 3.39 (d, 1H, J = 11.1 Hz), 3.23 (s, 3H), 3.11 (d, 1H, J = 11.1 Hz), 2.62 (dd, 1H, J = 5.5 Hz, J = 13.6 Hz), 2.33 (d, 1H, J = 13.4 Hz), 1.55 (d, 3H, J = 6.5 Hz).
22. 1 = 3.71% APEX2 v.1.0-22 User Manual, Bruker AXS Inc., Madison WI 53719, 2004.SAINT+v.6.02 User Manual, Bruker AXS Inc., Madison WI 53719, 1999.G.M.Scheldrick, SADABS, Program for Empirical Absorption Correction of Area Detector Data, University of Göttingen, 1996.G.M.Scheldrick, SHELXTL v. 5.10 Bruker AXS Inc., Madison WI 53719, 1999. Crystallographic data for (21) have been deposited with the Cambridge Crystallographic Data Centre, deposition number CCDC 821991.
23. T.G. Back, D.L. Baron, and K. Yang J. Org. Chem. 58 1993 2407
24. T. Matsuura, L.E. Overman, and D.J. Poon J. Am. Chem. Soc. 120 1998 6500 Also see references cited there in
25. Y. Ueno, C. Tanaka, and M. Okawara Chem. Lett. 1983 795