Systematic investigation on the synthesis of androstane-based 3-, 11- and 17-carboxamides via palladium-catalyzed aminocarbonylation

Steroids

Volumn 76, Issue 3, 2011, Pages 280-290

  Ács, Péter ^a   Takács, Attila ^a   Kiss, Mercédesz ^a   Pálinkás, Noémi ^a   Mahó, Sándor ^b   Kollár, László ^a  

^a UNIVERSITY OF PÉCS   (Hungary)

^b GEDEON RICHTER LTD   (Hungary)

Author keywords

Androstane; Carbonylation; Carboxamide; Iodo alkene; Palladium catalyst

Indexed keywords

11 CARBOXAMIDOANDROST 5,9(11) DIEN 3,17 DIONE; 17 CARBOXAMIDOANDROST 4,16 DIEN 3 ONE; 3 CARBOXAMIDOANDROST 3,5 DIEN 17 ONE; 3,17 DICARBOXAMIDOANDROST 3,5,16 TRIENE; ACETAL DERIVATIVE; AMIDE; ANDROSTANE DERIVATIVE; GUANIDINE DERIVATIVE; HYDRAZONE DERIVATIVE; IODINE; PALLADIUM; UNCLASSIFIED DRUG;

AMINOCARBONYLATION; ARTICLE; CARBONYLATION; CATALYSIS; CHEMICAL REACTION; SYNTHESIS;

AMIDES; ANDROSTANES; CATALYSIS; GUANIDINES; IODIDES; PALLADIUM;

EID: 78751649251     PISSN: 0039128X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.steroids.2010.11.008     Document Type: Article

References (26)

1. B. Cornils, W.A. Herrmann, Applied homogeneous catalysis with organometallic compounds 1996 Wiley-VCH Weinheim
2. M. Beller, C. Bolm, Transition metals for organic synthesis, vol. I-II 1998 Wiley-VCH Weinheim
3. I. Omae Applications of organometallic compounds 1998 Wiley New York
4. R. Skoda-Földes, and L. Kollár Transition metal catalysed reactions in steroid synthesis Chem Rev 103 2003 4095 4129 [and references cited therein]
5. Holt DA, Levy MA, Metcalf BW. Smithkline Beecham Co.; EP. 0 343 954 A2, 1989 [Chem. Abstr. 1990, 112, 198890n].
6. S. Cacchi, P.G. Ciattini, E. Morera, and G. Ortar Palladium-catalyzed carbonylation of aryl triflates. Synthesis of arenecarboxylic acid derivatives from phenols Tetrahedron Lett 27 1986 3931 3934
7. R.E. Dolle, S.J. Schmidt, and L.I. Kruse Palladium catalysed alkoxycarbonylation of phenols to benzoate esters Chem Commun 1987 904 905
8. D.A. Holt, M.A. Levy, D.L. Ladd, H. Oh, J.M. Erb, and J.I. Heaslip Steroidal A ring aryl carboxylic acids: a new class of steroid 5α-reductase inhibitors J Med Chem 33 1990 937 942
9. W. Tian, Z. Lei, L. Chen, and Y. Huang Some new reactions of poly(per)fluoroalkanesulfonyl fluorides with steroidal molecules J Fluorine Chem 101 2000 305 308
10. M.A. McGuire, E. Sorenson, D.N. Klein, and N.H. Baine Palladium and nickel catalyzed hydroxycarbonylation of a steroidal bromodiene in the synthesis of episteride, a potent 5α-reductase inhibitor Synth Commun 28 1998 1611 1615
11. A. Petz, G. Gálik, J. Horváth, Z. Tuba, Z. Berente, and Z. Pintér Facile, high-yielding synthesis of steroidal crown ethers via palladium-catalysed carbonylation reaction Synth Commun 31 2001 335 341
12. P. Duarte-Guterman, and V.L. Trudeau Regulation of thyroid hormone-, oestrogen- and androgen-related genes by triiodothyronine in the brain of silurana tropicals J Neuroendocrinol 22 2010 1023 1031
13. Chaudhary, U.B. Turner, and J.S. Finasteride Exp Opin Drug Metab 6 2010 873 881 [and references cited therein]
14. N. Duborija-Kovacevic, V. Jakovljevic, A. Sabo, and Z. Tomic Anti-nociceptive and anti-inflammatory properties of 5α-reductase inhibitor finasteride in experimental animals Eur J Drug Metab Ph 33 2008 181 186
15. T.C. Shao, H. Li, M. Ittmann, and G.R. Cunningham Effects of dutasteride on prostate growth in the large probasin-large T antigen mouse model of prostate cancer J Urol 178 2007 1521 1527 [and references cited therein]
16. P. Ács, E. Müller, G. Czira, S. Mahó, M. Pereira, and L. Kollár Facile synthesis of 12-carboxamido-11-spirostenes via palladium-catalyzed carbonylation reactions Steroids 71 2006 875 879
17. P. Ács, B. Jakab, A. Takács, and L. Kollár Facile synthesis of 11-carboxamido-androst-4,9(11)-dienes via palladium-catalyzed aminocarbonylation Steroids 72 2007 627 632
18. E. Stephan, M. Brossat, V. Lecomte, and P-A. Bouit Synthesis of the 11β-hydroxymethyl-androst-4-en-3,17-dione Tetrahedron 62 2006 2052 2055
19. V. Lecomte, E. Stephan, and G. Jaouen Access to 11β-ethynyl-androst- 5-ene Tetrahedron Lett 46 2005 1123 1126
20. V. Lecomte, E. Stephan, J. Vaissermann, and G. Jaouen Addition of aryllithium to an 11-oxo-steroid Tetrahedron Lett 42 2001 5409 5411
21. V. Lecomte, E. Stephan, F. Le Bideau, and G. Jaouen Improved addition of organolithium reagents to hindered and/or enolisable ketones Tetrahedron 59 2003 2169 2176
22. V. Lecomte, E. Stephan, J. Vaissermann, and G. Jaouen Are the 11-oxo-steroids really so hindered towards organometallic compounds? Steroids 69 2004 17 21
23. H.L. Herzog, M.A. Jevnik, M.E. Tully, and E.B. Hershberg Cyclic ketals of 4-androstene-3,17-dione J Am Chem Soc 75 1953 4425 4427
24. D.H.R. Barton, R.E. O'Brien, and S. Sternhell A new reaction of hydrazone's J Chem Soc 1962 470 476
25. D.H.R. Barton, B. Bashiardes, and J.L. Fourrey An improved preparation of vinyl iodides Tetrahedron Lett 24 1983 1605 1608
26. Z. Csákai, R. Skoda-Földes, and L. Kollár NMR investigation of Pd(II)-Pd(0) reduction in the presence of mono- and ditertiary phosphines Inorg Chim Acta 286 1999 93 97 [and references cited therein]