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Volumn 110, Issue 10, 1988, Pages 3318-3319

Silylation-mediated oxidation of 4-aza-3-ketosteroids with DDQ proceeds via DDQ-substrate adducts

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EID: 0001002591     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00218a062     Document Type: Article
Times cited : (71)

References (8)
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    • Rasmusson, G. H.; Reynolds, G. F.; Utne, T.; Jobson, R. B.; Primka, R. L.; Berman, C.; Brooks, J. R. J. Med. Chem. 1984, 27, 1690–1701. (b) Rasmusson, G. H.; Reynolds, G. F.; Steinberg, N. G.; Walton, E.; Patel, G. F.; Liang, T.; Cascieri, M. A.; Cheung, A. H.; Brooks, J. R.; Berman, C. J. Med. Chem. 1986, 29, 2298–2315.
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  • 2
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    • Magnus, P.; Pappalardo, P. A. J. Am. Chem. Soc. 1986, 108, 212–217. (b) Sharpless, K. B.; Lauer, R. F. J. Am. Chem. Soc. 1973, 95, 2697–2699. (c) Reich, H. J.; Reich, I. L.; Renga, J. M. J. Am. Chem. Soc. 1973, 95, 5813-5815; 1975, 97, 5434–5447. (d) Back, T. G. J. Org. Chem. 1981, 46, 1442–1446. (e) Trost, B. M.; Salzmann, T. M.; Hrirori, K. J. Am. Chem. Soc. 1976, 98, 4887–4902.
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    • Magnus, P.1    Pappalardo, P.A.2
  • 3
    • 85021516685 scopus 로고
    • (b) Rasmusson, G. H.; Johnston, D. B. R.; Arth, G. E. U.S. Patent 4 377 584, 1983
    • Rasmusson, G. H.; Johnston, D. B. R.; Reinhold, D. F.; Utne, T.; Jobson, R. B. U.S. Patent 4 220 775, 1980. (b) Rasmusson, G. H.; Johnston, D. B. R.; Arth, G. E. U.S. Patent 4 377 584, 1983.
    • (1980) U.S. Patent , vol.4 , Issue.775 , pp. 220
    • Rasmusson, G.H.1    Johnston, D.B.R.2    Reinhold, D.F.3    Utne, T.4    Jobson, R.B.5
  • 4
    • 49149141788 scopus 로고
    • 13C studies. Silicon-29 observations were made with the INEPT technique for optimum sensitivity. In the NMR studies a slight excess of DDQ was used, and BSTFA was added last
    • 13C studies. Silicon-29 observations were made with the INEPT technique (Burum, D. P.; Ernst, R. R. J. Magn. Reson. 1980, 39, 163–168) for optimum sensitivity. In the NMR studies a slight excess of DDQ was used, and BSTFA was added last.
    • (1980) J. Magn. Reson. , vol.39 , pp. 163-168
    • Burum, D.P.1    Ernst, R.R.2
  • 7
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    • 989–994. (b) Becker, H.-D. J. Am. Chem. Soc. 1969, 34, 1198–1210, 1211–1215. (c) Walker, D.; Hiebert, J. D. Chem. Rev. 1967, 67, 153–195. (d) Fu, P. P.; Harvey, R. G. Chem. Rev. 1978, 78, 317–361. (e) Turner, A. B. Synth. Reagent; 1977, 3, pp 194–228
    • Becker, H.-D. J. Org. Chem. 1965, 30, 982–989, 989–994. (b) Becker, H.-D. J. Am. Chem. Soc. 1969, 34, 1198–1210, 1211–1215. (c) Walker, D.; Hiebert, J. D. Chem. Rev. 1967, 67, 153–195. (d) Fu, P. P.; Harvey, R. G. Chem. Rev. 1978, 78, 317–361. (e) Turner, A. B. Synth. Reagent; 1977, 3, pp 194–228.
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    • (b) Jung, M. E.; Pan, Y.-G.; Rathke, M. W.; Sullivan, D. F.; Woodbury, R. P. J. Org. Chem. 1977, 42, 3961–3963. (c) Ryv, I.; Murai, S.; Hatayame, Y.; Sonoda, N. Tetrahedron Lett. 1978, 3455–3458
    • Fleming, I.; Paterson, I. Synthesis 1979, 736-738. (b) Jung, M. E.; Pan, Y.-G.; Rathke, M. W.; Sullivan, D. F.; Woodbury, R. P. J. Org. Chem. 1977, 42, 3961–3963. (c) Ryv, I.; Murai, S.; Hatayame, Y.; Sonoda, N. Tetrahedron Lett. 1978, 3455–3458.
    • (1979) Synthesis , pp. 736-738
    • Fleming, I.1    Paterson, I.2


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