메뉴 건너뛰기




Volumn 71, Issue 1, 2006, Pages 30-33

An efficient one-pot synthesis generating 4-ene-3,6-dione functionalised steroids from steroidal 5-en-3β-ols using a modified Jones oxidation methodology

Author keywords

4 Ene 3,6 dione; Aromatase inhibitor; Jones oxidation; One pot synthesis

Indexed keywords

13ALPHA ANDROST 4 ENE 3,6,17 TRIONE; ANDROST 4 ENE 3,6 DIONE; ANDROST 4 ENE 3,6,17 TRIONE; CHOLEST 4 ENE 3,6 DIONE; PREGNA 4 ENE 3,6,20 TRIONE; PREGNA 4,16 DIENE 3,6,20 TRIONE; STEROID; UNCLASSIFIED DRUG;

EID: 28544438916     PISSN: 0039128X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.steroids.2005.07.007     Document Type: Article
Times cited : (28)

References (23)
  • 1
    • 0029000440 scopus 로고
    • A novel chemical synthesis and carbon-13 nuclear magnetic resonance spectral properties of cholest-4-ene-3,6-dione
    • E.J. Parish, S.A. Kizito, J. Peng, R.W. Heidepriem, and P. Livant A novel chemical synthesis and carbon-13 nuclear magnetic resonance spectral properties of cholest-4-ene-3,6-dione Chem Phys Lipids 76 1995 129 133
    • (1995) Chem Phys Lipids , vol.76 , pp. 129-133
    • Parish, E.J.1    Kizito, S.A.2    Peng, J.3    Heidepriem, R.W.4    Livant, P.5
  • 2
    • 0021026437 scopus 로고
    • Occurrence and seasonal variation of 19-norcholest-4-en-3-one and 3β-monohydroxy sterols in Californian Gorgonian, Muricea californica
    • S. Popov, M.K. Carlson, and C. Djerassi Occurrence and seasonal variation of 19-norcholest-4-en-3-one and 3β-monohydroxy sterols in Californian Gorgonian, Muricea californica Steroids 41 1983 537 543
    • (1983) Steroids , vol.41 , pp. 537-543
    • Popov, S.1    Carlson, M.K.2    Djerassi, C.3
  • 3
    • 0000149849 scopus 로고
    • Anthosterones a and B, ring a contracted steroids from the sponge Anthoracuata graceae
    • M. Tischler, S.W. Ayer, R.J. Andersen, J.F. Mitchell, and J. Clardy Anthosterones A and B, ring A contracted steroids from the sponge Anthoracuata graceae Can J Chem 66 1988 1173 1178
    • (1988) Can J Chem , vol.66 , pp. 1173-1178
    • Tischler, M.1    Ayer, S.W.2    Andersen, R.J.3    Mitchell, J.F.4    Clardy, J.5
  • 4
    • 0026084892 scopus 로고
    • Steroids of the marine sponge Cinachyra tarentinaII isolation of cholest-4-ene-3,6-dione and (24R)-24-ethylcholest-4-ene-3,6-dione
    • A. Aello, E. Fattorusso, S. Magno, M. Menna, and M. Pansini Steroids of the marine sponge Cinachyra tarentinaII isolation of cholest-4-ene-3,6-dione and (24R)-24-ethylcholest-4-ene-3,6-dione J Nat Prod 54 1991 281 285
    • (1991) J Nat Prod , vol.54 , pp. 281-285
    • Aello, A.1    Fattorusso, E.2    Magno, S.3    Menna, M.4    Pansini, M.5
  • 5
    • 0032005475 scopus 로고    scopus 로고
    • Steroidal 5-en-3-ones, intermediates of the transformation of steroidal 5-en-3β-ols to steroidal 4-en-3,6-diones oxidized by pyridinium dichromate and pyridinium chlorochromate
    • S.-H. Li, and T.S. Li Steroidal 5-en-3-ones, intermediates of the transformation of steroidal 5-en-3β-ols to steroidal 4-en-3,6-diones oxidized by pyridinium dichromate and pyridinium chlorochromate Steroids 63 1998 76 79
    • (1998) Steroids , vol.63 , pp. 76-79
    • Li, S.-H.1    Li, T.S.2
  • 7
    • 0035912880 scopus 로고    scopus 로고
    • Aromatase inhibitors: Past, present and future
    • G.-E. Séralini, and S. Moslemi Aromatase inhibitors: past, present and future Mol Cell Endocrinol 178 2001 117 131
    • (2001) Mol Cell Endocrinol , vol.178 , pp. 117-131
    • Séralini, G.-E.1    Moslemi, S.2
  • 8
    • 16644378819 scopus 로고    scopus 로고
    • C(10)-C(19) bond cleavage reaction of 19-oxygenated androst-4-ene-3,6- dione steroids under various conditions
    • M. Nagaoka, and M. Numazawa C(10)-C(19) bond cleavage reaction of 19-oxygenated androst-4-ene-3,6-dione steroids under various conditions Chem Pharm Bull 52 2004 983 985
    • (2004) Chem Pharm Bull , vol.52 , pp. 983-985
    • Nagaoka, M.1    Numazawa, M.2
  • 9
    • 0028029903 scopus 로고
    • A- or B-Ring-substituted derivatives of androst-4-ene-3,6,17-trione as aromatase inhibitors. Structure-activity relationships
    • M. Numazawa, and M. Tachibana A- or B-Ring-substituted derivatives of androst-4-ene-3,6,17-trione as aromatase inhibitors. Structure-activity relationships Steroids 59 1994 579 585
    • (1994) Steroids , vol.59 , pp. 579-585
    • Numazawa, M.1    Tachibana, M.2
  • 11
    • 0026785214 scopus 로고
    • Selective oxidation of steroidal homoallylic alcohols using pyridinium chlorochromate (PPC)
    • E.J. Parish, C. Luo, S. Parish, and R.W. Heidepriem Selective oxidation of steroidal homoallylic alcohols using pyridinium chlorochromate (PPC) Synth Commun 22 1992 2839 2847
    • (1992) Synth Commun , vol.22 , pp. 2839-2847
    • Parish, E.J.1    Luo, C.2    Parish, S.3    Heidepriem, R.W.4
  • 12
    • 0028354284 scopus 로고
    • Oxidation of steroidal 5-en-3β-ols with Jones reagent in ether
    • B.A. Šolaja, D.R. Milić, and L.I. Došen- Mićović Oxidation of steroidal 5-en-3β-ols with Jones reagent in ether Steroids 59 1994 330 334
    • (1994) Steroids , vol.59 , pp. 330-334
    • Šolaja, B.A.1    Milić, D.R.2    Došen-Mićović, L.I.3
  • 13
    • 0030022975 scopus 로고    scopus 로고
    • 5-3-ols using pyridinium chlorochromate
    • 5-3-ols using pyridinium chlorochromate Synth Commun 26 1996 225 230
    • (1996) Synth Commun , vol.26 , pp. 225-230
    • Nagia, A.1    Anthony, A.2
  • 15
    • 0033105263 scopus 로고    scopus 로고
    • Improved syntheses of aromatase inhibitors and neuroactive steroids efficient oxidations and reductions at key positions for bioactivity
    • A.S.C. Neves, M.L. Sá Melo, M.J.S.M. Moreno, E.J.T. da Silva, A.R. Salvador, and S.P. da Costa Improved syntheses of aromatase inhibitors and neuroactive steroids efficient oxidations and reductions at key positions for bioactivity Tetrahedron 55 1999 3255 3264
    • (1999) Tetrahedron , vol.55 , pp. 3255-3264
    • Neves, A.S.C.1    Sá Melo, M.L.2    Moreno, M.J.S.M.3    Da Silva, E.J.T.4    Salvador, A.R.5    Da Costa, S.P.6
  • 16
    • 33646109252 scopus 로고
    • Researches on acetylenic compounds. Part 1. the preparation of acetylenic ketones by oxidation of acetylenic carbinols and glycols
    • K. Bowden, I.M. Heilbron, E.R.H. Jones, and BC.L. Weedon Researches on acetylenic compounds. Part 1. The preparation of acetylenic ketones by oxidation of acetylenic carbinols and glycols J Chem Soc 1946 39 45
    • (1946) J Chem Soc , pp. 39-45
    • Bowden, K.1    Heilbron, I.M.2    Jones, E.R.H.3    Weedon, B.L.4
  • 17
    • 19444382188 scopus 로고    scopus 로고
    • Fate of novel quasi reverse steroidal substrates by Aspergillus tamarii KITA: Bypass of lactonisation and an exclusive role for the minor hydroxylation pathway
    • A.C. Hunter, S. Kennedy, S.J. Clabby, and J. Elsom Fate of novel quasi reverse steroidal substrates by Aspergillus tamarii KITA: bypass of lactonisation and an exclusive role for the minor hydroxylation pathway Biochim Biophys Acta 1734 2005 190 197
    • (2005) Biochim Biophys Acta , vol.1734 , pp. 190-197
    • Hunter, A.C.1    Kennedy, S.2    Clabby, S.J.3    Elsom, J.4
  • 19
    • 37049081387 scopus 로고
    • 1H NMR spectra of steroidal hormones, their hydroxylated derivatives and related compounds
    • 1H NMR spectra of steroidal hormones, their hydroxylated derivatives and related compounds J Chem Soc Perkin Trans 2 9 1990 1567 1594
    • (1990) J Chem Soc Perkin Trans , vol.2 , Issue.9 , pp. 1567-1594
    • Kirk, D.N.1    Toms, H.C.2    Douglas, C.3    White, K.A.4
  • 20
    • 84986738357 scopus 로고
    • 13C NMR spectra of steroids - A survey and commentary
    • 13C NMR spectra of steroids - a survey and commentary Org Mag Res 9 1977 439 463
    • (1977) Org Mag Res , vol.9 , pp. 439-463
    • Blunt, J.W.1    Stothers, J.B.2
  • 21
    • 28544444104 scopus 로고
    • Oxydations par le carbonate d'argent sur celite-X: Oxydations de triols en serie androstane
    • M. Fetizon, and P. Mourgues Oxydations par le carbonate d'argent sur celite-X: oxydations de triols en serie androstane Tetrahedron 30 1974 327 335
    • (1974) Tetrahedron , vol.30 , pp. 327-335
    • Fetizon, M.1    Mourgues, P.2
  • 22
    • 0015270544 scopus 로고
    • Aromatization of some 4,5-epoxy-3-hydroxysteroids
    • D. Baldwin, and J.R. Hanson Aromatization of some 4,5-epoxy-3- hydroxysteroids J Chem Soc Perkin Trans 1 1972 1889 1891
    • (1972) J Chem Soc Perkin Trans , vol.1 , pp. 1889-1891
    • Baldwin, D.1    Hanson, J.R.2
  • 23
    • 0347362546 scopus 로고    scopus 로고
    • Flexibility of the endogenous progesterone lactonisation pathway in Aspergillus Tamarii KITA: Transformation of a series of cortical steroid analogues
    • A.C. Hunter, and N.E. Carragher Flexibility of the endogenous progesterone lactonisation pathway in Aspergillus Tamarii KITA: transformation of a series of cortical steroid analogues J Steroid Biochem Mol Biol 87 2003 301 308
    • (2003) J Steroid Biochem Mol Biol , vol.87 , pp. 301-308
    • Hunter, A.C.1    Carragher, N.E.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.