Facile synthesis of 11-carboxamido-androst-4,9(11)-dienes via palladium-catalyzed aminocarbonylation

Steroids

Volumn 72, Issue 8, 2007, Pages 627-632

  Ács, Péter ^a   Jakab, Balázs ^a   Takács, Attila ^a   Kollár, László ^a  

^a UNIVERSITY OF PÉCS   (Hungary)

Author keywords

Androstane; Carbonylation; Carboxamide; Iodo alkene; Palladium catalyst

Indexed keywords

11 CARBOXAMIDOANDROST 4,9(11) DIENE DERIVATIVE; ALIPHATIC AMINE; AMIDE; AMINO ACID DERIVATIVE; ANDROSTANE DERIVATIVE; AROMATIC AMINE; CARBONYL DERIVATIVE; HYDRAZONE DERIVATIVE; KETONE DERIVATIVE; PALLADIUM; STEROID; UNCLASSIFIED DRUG;

ARTICLE; CARBONYLATION; CATALYSIS; CATALYST; CHEMICAL REACTION; QUANTUM YIELD; REACTION ANALYSIS; SYNTHESIS;

ALKENES; ANDROSTADIENES; CARBON; CATALYSIS; MOLECULAR CONFORMATION; MOLECULAR STRUCTURE; PALLADIUM; POLYENES; STEROIDS;

EID: 34250897340     PISSN: 0039128X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.steroids.2007.04.004     Document Type: Article

References (17)

1. In: Cornils B., and Herrmann W.A. (Eds). Applied homogeneous catalysis with organometallic compounds (1996), Wiley-VCH, Weinheim
2. In: Beller M., and Bolm C. (Eds). Transition metals for organic synthesis vols. I-II (1998), Wiley-VCH, Weinheim
3. Omae I. Applications of organometallic compounds (1998), Wiley, New York
4. Skoda-Földes R., and Kollár L. Transition metal catalysed reactions in steroid synthesis. Chem Rev 103 (2003) 4095-4129 [and references cited therein]
5. Holt DA, Levy MA, Metcalf BW, inventors. Smithkline Beecham Co., EP. 0,343,954 A2; 1989 [Chem. Abstr. 1990, 112, 198890n].
6. Cacchi S., Ciattini P.G., Morera E., and Ortar G. Palladium-catalyzed carbonylation of aryl triflates. Synthesis of arenecarboxylic acid derivatives from phenols. Tetrahedron Lett 27 (1986) 3931-3934
7. Dolle R.E., Schmidt S.J., and Kruse L.I. Palladium catalysed alkoxycarbonylation of phenols to benzoate esters. Chem Commun (1987) 904-905
8. Holt D.A., Levy M.A., Ladd D.L., Oh H., Erb J.M., Heaslip J.I., Brandt M., and Metcalf B.W. Steroidal A ring aryl carboxylic acids: a new class of steroid 5α-reductase inhibitors. J Med Chem 33 (1990) 937-942
9. Tian W., Lei Z., Chen L., and Huang Y. Some new reactions of poly(per)fluoroalkanesulfonyl fluorides with steroidal molecules. J Fluorine Chem 101 (2000) 305-308
10. McGuire M.A., Sorenson E., Klein D.N., and Baine N.H. 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. Petz A., Gálik G., Horváth J., Tuba Z., Berente Z., Pintér Z., and Kollár L. Facile, high-yielding synthesis of steroidal crown ethers via palladium-catalysed carbonylation reaction. Synth Commun 31 (2001) 335-341
12. Ács P., Müller E., Czira G., Mahó S., Pereira M., and Kollár L. Facile synthesis of 12-carboxamido-11-spirostenes via palladium-catalyzed carbonylation reactions. Steroids 71 (2006) 875-879
13. di Chenna P.H., Ferrara A., Ghini A.A., and Burton G. Cleavage of cyclopropyl ketones mediated by alkylmercury(II) hydrides. J Chem Soc Perkin Trans 1 (2002) 227-231
14. Sondheimer F., Baters E., and Rosenkranz G. Steroids. LXXXVI. Synthesis of monofunctional 11-ketones. J Am Chem Soc 70 (1948) 1090-1092
15. Barton D.H.R., O'Brien R.E., and Sternhell S. A new reaction of hydrazone's. J Chem Soc (1962) 470-476
16. Barton D.H.R., Bashiardes B., and Fourrey J.L. An improved preparation of vinyl iodides. Tetrahedron Lett 24 (1983) 1605-1608
17. Csákai Z., Skoda-Földes R., and Kollár L. 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]