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Synthesis 2005(10): 1578-1580
DOI: 10.1055/s-2005-865287
DOI: 10.1055/s-2005-865287
SHORTPAPER
© Georg Thieme Verlag Stuttgart · New York
A Facile Synthesis of 4- and 6-Aryl-Substituted Steroids by the Suzuki-Miyaura Cross-Coupling Reaction
Further Information
Received
25 November 2004
Publication Date:
07 April 2005 (online)
Publication History
Publication Date:
07 April 2005 (online)
Abstract
Potential aromatase inhibitors - 4- and 6-aryl-substituted derivatives of androst-4-ene-3,17-dione and 17-hydroxyprogesterone - have been prepared by the Suzuki-Miyaura cross-coupling from their corresponding 4- and 6-bromosteroids.
Key words
cross-coupling - palladium - steroids - Suzuki reaction - arylation
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1a
Lonning PE. Int. J. Clin. Oncol. 2002, 7: 265 -
1b
Mokbel K. Int. J. Clin. Oncol. 2002, 7: 279 - 2
Lonning PE. Eur. J. Cancer 2002, 38: S47 -
3a
Brodie AMH.Schwarzel WC.Shaikh AA.Brodie HJ. Endocrinology 1977, 100: 1684 -
3b
Hervey HA.Lipton A.Santen RJ. Cancer Res. 1982, 42: 3261 ; (Suppl.) -
3c
Henderson D. J. Steroid Biochem. Mol. Biol. 1987, 27: 905 -
3d
Covey DF. In Steroid Biosynthesis Inhibitors: Pharmaceutical and Agrochemical AspectsBerg D.Plemel M. Ellis Horwood Ltd.; Chichester: 1988. p.534 -
3e
Banting L.Nicholls PJ.Shaw MA.Smith HJ. In Progress in Medicinal Chemistry Vol. 26:Ellis GP.West GB. Elsevier; Amsterdam: 1989. p.253 -
3f
Bossche HV. J. Steroid Biochem. Mol. Biol. 1992, 43: 1003 -
3g
Brodie AMH.Santen RJ. Breast Cancer Res. Treat. 1994, 30: 1 - 4
Brodie AMH. J. Steroid Biochem. Mol. Biol. 1994, 49: 281 - 5
Kerb U,Sauer G,Wiechert R,Henderson D,Nishino Y, andBeier S. inventors; Ger. Offen. DE 3322285. ; Chem. Abstr. 1985, 102, 204169w - 6
Levina IS. Russ. Chem. Rev. 1998, 67: 975 - 7
Skoda-Foldes R.Kollar L. Chem. Rev. 2003, 103: 4095 -
8a
Scoda-Foldes R.Kollar L.Balint H.Galik G.Tuba Z.Arcadi A. Tetrahedron: Asymmetry 1991, 2: 633 -
8b
Kollar L.Scoda-Foldes R.Maho S.Tuba Z. J. Organomet. Chem. 1993, 453: 159 -
8c
Gravett EC.Hilton PJ.Jones K.Romero F. Tetrahedron Lett. 2001, 42: 9081 -
8d
Tuozzi A.Sterzo CL.Sperandio GB. Tetrahedron 1999, 55: 461 -
9a
Jeges G.Scoda-Foldes R.Kollar L.Pinter Z.Horvath J.Tuba Z. J. Mol. Catal. A: Chem. 2001, 165: 89 -
9b
Scoda-Foldes R.Horvath J.Tuba Z.Kollar L. J. Organomet. Chem. 1999, 586: 94 -
10a
Stang PJ.Treptow W. Synthesis 1984, 283 -
10b
Stang PJ.Fisk TE. Synthesis 1979, 438 -
11a
Barton HR.Bashiardes G.Fourrey J. Tetrahedron 1988, 44: 147 -
11b
Skoda-Foldes R.Kollar L.Horvath J.Tuba Z. Steroids 1995, 60: 791 -
11c
Schweder B.Uhlig E. J. Prakt. Chem. 1991, 333: 223 -
12a
Hodson HF.Madge DJ.Widdowson DA. J. Chem. Soc., Perkin Trans. 1 1995, 2965 -
12b
Kirk DN.Patel DK.Petrow V. J. Chem. Soc. 1956, 627 -
13a
Suzuki AJ. J. Organomet. Chem. 2002, 653: 83 -
13b
Miyaura N. Top. Curr. Chem. 2002, 219: 11 -
13c
Suzuki AJ. J. Organomet. Chem. 1999, 576: 147 -
13d
Miyaura N.Suzuki AJ. Chem. Rev. 1995, 95: 2457 -
13e
Beletskaya IP.Cheprakov AV. In Comprehensive Coordination Chemistry II Vol. 9:Meyer TJ.McCleverty JA. Elsevier; Amsterdam: 2004. p.305