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Volumn 74, Issue 4-5, 2009, Pages 419-423

The synthesis of 13α-androsta-5,16-diene derivatives with carboxylic acid, ester and carboxamido functionalities at position-17 via palladium-catalyzed carbonylation

Author keywords

13 steroid; Carbonylation; Carboxamide; Iodoalkene; Palladium; Steroid

Indexed keywords

13 ALPHA ANDROSTA 5,16 DIENE; ALKADIENE; AMIDE; ANDROSTANE DERIVATIVE; CARBONYL DERIVATIVE; CARBOXYLIC ACID; CARBOXYLIC ACID DERIVATIVE; ESTER; HYDRAZONE DERIVATIVE; PALLADIUM; UNCLASSIFIED DRUG; WATER;

EID: 61349190922     PISSN: 0039128X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.steroids.2008.12.009     Document Type: Article
Times cited : (17)

References (29)
  • 1
    • 85015470014 scopus 로고
    • A new one-pot synthesis of 17-oxo-13α-steroids of androstane series from their 13β-analogues
    • Yaremenko F.G., and Khvat A.V. A new one-pot synthesis of 17-oxo-13α-steroids of androstane series from their 13β-analogues. Mendeleev Commun 4 (1994) 187-188
    • (1994) Mendeleev Commun , vol.4 , pp. 187-188
    • Yaremenko, F.G.1    Khvat, A.V.2
  • 4
    • 0000820601 scopus 로고
    • Conformational analysis of epimeric 16-bromo-13α-estrones
    • Nambara T., Kudo T., Hosoda H., Motojima K., and Goya S. Conformational analysis of epimeric 16-bromo-13α-estrones. Chem Pharm Bull 17 (1969) 2366-2370
    • (1969) Chem Pharm Bull , vol.17 , pp. 2366-2370
    • Nambara, T.1    Kudo, T.2    Hosoda, H.3    Motojima, K.4    Goya, S.5
  • 5
    • 85007995154 scopus 로고
    • The synthesis and conformational analysis of α-bromo-16-ketones of 13α-estratriene
    • Nambara T., and Kudo T. The synthesis and conformational analysis of α-bromo-16-ketones of 13α-estratriene. Chem Pharm Bull 20 (1972) 2156-2162
    • (1972) Chem Pharm Bull , vol.20 , pp. 2156-2162
    • Nambara, T.1    Kudo, T.2
  • 6
    • 33646769927 scopus 로고    scopus 로고
    • Synthesis and stereochemical investigations of novel nitrogen-containing 13α-estrone derivatives
    • Mernyák E., Schneider G., Herbst-Irmer R., Kubas M., and Wölfling J. Synthesis and stereochemical investigations of novel nitrogen-containing 13α-estrone derivatives. Steroids 71 (2006) 558-564
    • (2006) Steroids , vol.71 , pp. 558-564
    • Mernyák, E.1    Schneider, G.2    Herbst-Irmer, R.3    Kubas, M.4    Wölfling, J.5
  • 7
    • 38949196459 scopus 로고    scopus 로고
    • δ-alkenyl oximes as ambident nucleophiles: electrophile-induced formation of oxazepane derivatives in the bis-estrone series
    • Mernyák E., Bikádi Z., Hazai E., Márk L., Schneider G., Wölfling J., and Steroidal. δ-alkenyl oximes as ambident nucleophiles: electrophile-induced formation of oxazepane derivatives in the bis-estrone series. Lett Org Chem 5 (2008) 17-21
    • (2008) Lett Org Chem , vol.5 , pp. 17-21
    • Mernyák, E.1    Bikádi, Z.2    Hazai, E.3    Márk, L.4    Schneider, G.5    Wölfling, J.6    Steroidal7
  • 8
    • 0016640560 scopus 로고
    • Analytical chemical studies on steroids. 77. Crystal structure of 3-methoxy-16-hydroxy-13-alpha-estra-1,3,5(10), 15-tetraen-17-one para-bromobenzoate
    • Nambara T., Kudo T., Hosoda H., Iitaka Y., and Kikutani N. Analytical chemical studies on steroids. 77. Crystal structure of 3-methoxy-16-hydroxy-13-alpha-estra-1,3,5(10), 15-tetraen-17-one para-bromobenzoate. Chem Pharm Bull 23 (1975) 320-325
    • (1975) Chem Pharm Bull , vol.23 , pp. 320-325
    • Nambara, T.1    Kudo, T.2    Hosoda, H.3    Iitaka, Y.4    Kikutani, N.5
  • 9
    • 85007905013 scopus 로고
    • A nuclear magnetic resonance spectral study of 5α,13α-androstanes
    • Nambara T., Hosoda H., and Usui M. A nuclear magnetic resonance spectral study of 5α,13α-androstanes. Chem Pharm Bull 17 (1969) 1687-1693
    • (1969) Chem Pharm Bull , vol.17 , pp. 1687-1693
    • Nambara, T.1    Hosoda, H.2    Usui, M.3
  • 11
    • 33750627797 scopus 로고    scopus 로고
    • The synthesis of D-heteroannulated 3β-hydroxy-13α-androst-5-ene derivatives via α-oxoketene dithioacetal and α-oxohydroxymethylidene synthons
    • Szájli A., and Wölfling J. The synthesis of D-heteroannulated 3β-hydroxy-13α-androst-5-ene derivatives via α-oxoketene dithioacetal and α-oxohydroxymethylidene synthons. Monats Chem 137 (2006) 1431-1440
    • (2006) Monats Chem , vol.137 , pp. 1431-1440
    • Szájli, A.1    Wölfling, J.2
  • 13
    • 10744221098 scopus 로고    scopus 로고
    • Transition-metal-catalyzed reactions in steroid synthesis
    • Skoda-Földes R., and Kollár L. Transition-metal-catalyzed reactions in steroid synthesis. Chem Rev 103 (2003) 4095-4129
    • (2003) Chem Rev , vol.103 , pp. 4095-4129
    • Skoda-Földes, R.1    Kollár, L.2
  • 14
    • 61349137154 scopus 로고    scopus 로고
    • Holt DA, Levy MA, Metcalf B.W., inventors; SmithKline Beecham Co.; EP. 0 343 954 A2, 1989. (Chem Abstr 1990; 112, 198890n).
    • Holt DA, Levy MA, Metcalf B.W., inventors; SmithKline Beecham Co.; EP. 0 343 954 A2, 1989. (Chem Abstr 1990; 112, 198890n).
  • 15
    • 0000628039 scopus 로고
    • Palladium-catalyzed carbonylation of aryl triflates, Synthesis of arenecarboxylic acid derivatives from phenols
    • 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
    • (1986) Tetrahedron Lett , vol.27 , pp. 3931-3934
    • Cacchi, S.1    Ciattini, P.G.2    Morera, E.3    Ortar, G.4
  • 16
    • 37049081210 scopus 로고
    • Palladium catalysed alkoxycarbonylation of phenols to benzoate esters
    • Dolle R.E., Schmidt S.J., and Kruse L.I. Palladium catalysed alkoxycarbonylation of phenols to benzoate esters. Chem Commun (1987) 904-905
    • (1987) Chem Commun , pp. 904-905
    • Dolle, R.E.1    Schmidt, S.J.2    Kruse, L.I.3
  • 18
    • 0000832931 scopus 로고    scopus 로고
    • Some new reactions of poly(per)fluoroalkanesulfonyl fluorides with steroidal molecules
    • 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
    • (2000) J Fluorine Chem , vol.101 , pp. 305-308
    • Tian, W.1    Lei, Z.2    Chen, L.3    Huang, Y.4
  • 19
    • 0031978238 scopus 로고    scopus 로고
    • Palladium and nickel catalyzed hydroxycarbonylation of a steroidal bromodiene in the synthesis of episteride, a potent 5α-reductase inhibitor
    • 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
    • (1998) Synth Commun , vol.28 , pp. 1611-1615
    • McGuire, M.A.1    Sorenson, E.2    Klein, D.N.3    Baine, N.H.4
  • 20
    • 0035083324 scopus 로고    scopus 로고
    • Facile, high-yielding synthesis of steroidal crown ethers via palladium-catalysed carbonylation reaction
    • 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
    • (2001) Synth Commun , vol.31 , pp. 335-341
    • Petz, A.1    Gálik, G.2    Horváth, J.3    Tuba, Z.4    Berente, Z.5    Pintér, Z.6    Kollár, L.7
  • 21
    • 33747843113 scopus 로고    scopus 로고
    • Facile synthesis of 12-carboxamido-11-spirostenes via palladium-catalyzed carbonylation reactions
    • 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
    • (2006) Steroids , vol.71 , pp. 875-879
    • Ács, P.1    Müller, E.2    Czira, G.3    Mahó, S.4    Pereira, M.5    Kollár, L.6
  • 22
    • 34250897340 scopus 로고    scopus 로고
    • Facile synthesis of 11-carboxamido-androst-4, 9(11)-dienes via palladium-catalyzed aminocarbonylation
    • Ács P., Jakab B., Takács A., and Kollár L. Facile synthesis of 11-carboxamido-androst-4, 9(11)-dienes via palladium-catalyzed aminocarbonylation. Steroids 72 (2007) 627-632
    • (2007) Steroids , vol.72 , pp. 627-632
    • Ács, P.1    Jakab, B.2    Takács, A.3    Kollár, L.4
  • 23
    • 41549159199 scopus 로고    scopus 로고
    • The synthesis of 17-alkoxycarbonyl- and 17-carboxamido-13α-estra-1,3,5(10), 16-tetraene derivatives via palladium-catalyzed carbonylation reactions
    • Ács P., Takács A., Szilágyi A., Wölfling J., Schneider G., and Kollár L. The synthesis of 17-alkoxycarbonyl- and 17-carboxamido-13α-estra-1,3,5(10), 16-tetraene derivatives via palladium-catalyzed carbonylation reactions. Steroids 73 (2008) 669-675
    • (2008) Steroids , vol.73 , pp. 669-675
    • Ács, P.1    Takács, A.2    Szilágyi, A.3    Wölfling, J.4    Schneider, G.5    Kollár, L.6
  • 26
    • 0039442773 scopus 로고    scopus 로고
    • NMR investigation of Pd(II)-Pd(0) reduction in the presence of mono- and ditertiary phosphines
    • and references cited therein
    • 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
    • (1999) Inorg Chim Acta , vol.286 , pp. 93-97
    • Csákai, Z.1    Skoda-Földes, R.2    Kollár, L.3
  • 28
    • 0042737909 scopus 로고    scopus 로고
    • 17α inhibitors: 17-(2′-oxazolyl)- and 17-(2′-thiazolyl)-androstene derivatives
    • 17α inhibitors: 17-(2′-oxazolyl)- and 17-(2′-thiazolyl)-androstene derivatives. Steroids 68 (2003) 603-611
    • (2003) Steroids , vol.68 , pp. 603-611
    • Zhu, N.1    Ling, Y.2    Lei, X.3    Handratta, V.4    Brodie, A.M.H.5
  • 29
    • 4544291964 scopus 로고    scopus 로고
    • Synthetic cardenolides and related compounds
    • Schneider G., and Wölfling J. Synthetic cardenolides and related compounds. Curr Org Chem 8 (2004) 1381-1403
    • (2004) Curr Org Chem , vol.8 , pp. 1381-1403
    • Schneider, G.1    Wölfling, J.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.