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Volumn 40, Issue 14, 1999, Pages 2849-2852

A trifunctional steroid-based scaffold for combinatorial chemistry

Author keywords

Combinatorial chemistry; Reduction; Steroids and sterols; X ray crystallography

Indexed keywords

CHOLIC ACID; STEROID;

EID: 0033515810     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)00309-3     Document Type: Article
Times cited : (47)

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    • See ref. l(a) and: (a) Boyce, R.; Li, G.; Nestler, H. P.; Suenaga, T.; Still, W. C. J. Am. Chem. Soc. 1994, 116, 7955; (b) Cheng, Y. A.; Suenaga, T.; Still, W. C. J. Am. Chem. Soc. 1996, 118, 1813; (c) Wess, G.; Bock, K.; Kleine, H.; Kurz, M.; Guba, W.; Hemmerle, H.; Lopez-Calle, E.; Baringhaus, K. H.; Glombik, H.; Enhsen, A.; Kramer, W. Angew. Chem., Int. Ed. Engl. 1996, 35, 2222; (d) Kasal, A.; Kohout, L.; Lebl, M. Coll. Czech. Chem. Comm. 1995, 60, 2147; (e) Broderick, S.; Davis, A. F.; Williams, R. P. Tetrahedron Lett. 1998, 39, 6083; (f) Kocis, P.; Issakova, O.; Sepetov, N. F.; Lebl, M. Tetrahedron Lett. 1995, 36, 6623; (g) Neustadt, B. R.; Smith, E. M.; Nechuta, T.; Zhang, Y. Z. Tetrahedron Lett. 1998, 39, 5317 (and refs. cited therein); (h) Wunberg, T.; Kallus, C.; Opatz, T.; Henke, S.; Schmidt, W.; Kunz, H. Angew. Chem., Int. Ed. Engl. 1998, 37, 2503 (and refs. cited therein); (i) Pryor, K. E.; Shipps, G. W.; Skyler, D. A.; Rebek, J. Tetrahedron 1998, 54, 4107 (and refs. cited therein); (j) Mink, D.; Mecozzi, S.; Rebek, J. Tetrahedron Lett. 1998, 39, 5709.
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    • See ref. l(a) and: (a) Boyce, R.; Li, G.; Nestler, H. P.; Suenaga, T.; Still, W. C. J. Am. Chem. Soc. 1994, 116, 7955; (b) Cheng, Y. A.; Suenaga, T.; Still, W. C. J. Am. Chem. Soc. 1996, 118, 1813; (c) Wess, G.; Bock, K.; Kleine, H.; Kurz, M.; Guba, W.; Hemmerle, H.; Lopez-Calle, E.; Baringhaus, K. H.; Glombik, H.; Enhsen, A.; Kramer, W. Angew. Chem., Int. Ed. Engl. 1996, 35, 2222; (d) Kasal, A.; Kohout, L.; Lebl, M. Coll. Czech. Chem. Comm. 1995, 60, 2147; (e) Broderick, S.; Davis, A. F.; Williams, R. P. Tetrahedron Lett. 1998, 39, 6083; (f) Kocis, P.; Issakova, O.; Sepetov, N. F.; Lebl, M. Tetrahedron Lett. 1995, 36, 6623; (g) Neustadt, B. R.; Smith, E. M.; Nechuta, T.; Zhang, Y. Z. Tetrahedron Lett. 1998, 39, 5317 (and refs. cited therein); (h) Wunberg, T.; Kallus, C.; Opatz, T.; Henke, S.; Schmidt, W.; Kunz, H. Angew. Chem., Int. Ed. Engl. 1998, 37, 2503 (and refs. cited therein); (i) Pryor, K. E.; Shipps, G. W.; Skyler, D. A.; Rebek, J. Tetrahedron 1998, 54, 4107 (and refs. cited therein); (j) Mink, D.; Mecozzi, S.; Rebek, J. Tetrahedron Lett. 1998, 39, 5709.
    • (1998) Tetrahedron Lett. , vol.39 , pp. 6083
    • Broderick, S.1    Davis, A.F.2    Williams, R.P.3
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    • See ref. l(a) and: (a) Boyce, R.; Li, G.; Nestler, H. P.; Suenaga, T.; Still, W. C. J. Am. Chem. Soc. 1994, 116, 7955; (b) Cheng, Y. A.; Suenaga, T.; Still, W. C. J. Am. Chem. Soc. 1996, 118, 1813; (c) Wess, G.; Bock, K.; Kleine, H.; Kurz, M.; Guba, W.; Hemmerle, H.; Lopez-Calle, E.; Baringhaus, K. H.; Glombik, H.; Enhsen, A.; Kramer, W. Angew. Chem., Int. Ed. Engl. 1996, 35, 2222; (d) Kasal, A.; Kohout, L.; Lebl, M. Coll. Czech. Chem. Comm. 1995, 60, 2147; (e) Broderick, S.; Davis, A. F.; Williams, R. P. Tetrahedron Lett. 1998, 39, 6083; (f) Kocis, P.; Issakova, O.; Sepetov, N. F.; Lebl, M. Tetrahedron Lett. 1995, 36, 6623; (g) Neustadt, B. R.; Smith, E. M.; Nechuta, T.; Zhang, Y. Z. Tetrahedron Lett. 1998, 39, 5317 (and refs. cited therein); (h) Wunberg, T.; Kallus, C.; Opatz, T.; Henke, S.; Schmidt, W.; Kunz, H. Angew. Chem., Int. Ed. Engl. 1998, 37, 2503 (and refs. cited therein); (i) Pryor, K. E.; Shipps, G. W.; Skyler, D. A.; Rebek, J. Tetrahedron 1998, 54, 4107 (and refs. cited therein); (j) Mink, D.; Mecozzi, S.; Rebek, J. Tetrahedron Lett. 1998, 39, 5709.
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    • and refs. cited therein
    • See ref. l(a) and: (a) Boyce, R.; Li, G.; Nestler, H. P.; Suenaga, T.; Still, W. C. J. Am. Chem. Soc. 1994, 116, 7955; (b) Cheng, Y. A.; Suenaga, T.; Still, W. C. J. Am. Chem. Soc. 1996, 118, 1813; (c) Wess, G.; Bock, K.; Kleine, H.; Kurz, M.; Guba, W.; Hemmerle, H.; Lopez-Calle, E.; Baringhaus, K. H.; Glombik, H.; Enhsen, A.; Kramer, W. Angew. Chem., Int. Ed. Engl. 1996, 35, 2222; (d) Kasal, A.; Kohout, L.; Lebl, M. Coll. Czech. Chem. Comm. 1995, 60, 2147; (e) Broderick, S.; Davis, A. F.; Williams, R. P. Tetrahedron Lett. 1998, 39, 6083; (f) Kocis, P.; Issakova, O.; Sepetov, N. F.; Lebl, M. Tetrahedron Lett. 1995, 36, 6623; (g) Neustadt, B. R.; Smith, E. M.; Nechuta, T.; Zhang, Y. Z. Tetrahedron Lett. 1998, 39, 5317 (and refs. cited therein); (h) Wunberg, T.; Kallus, C.; Opatz, T.; Henke, S.; Schmidt, W.; Kunz, H. Angew. Chem., Int. Ed. Engl. 1998, 37, 2503 (and refs. cited therein); (i) Pryor, K. E.; Shipps, G. W.; Skyler, D. A.; Rebek, J. Tetrahedron 1998, 54, 4107 (and refs. cited therein); (j) Mink, D.; Mecozzi, S.; Rebek, J. Tetrahedron Lett. 1998, 39, 5709.
    • (1998) Tetrahedron Lett. , vol.39 , pp. 5317
    • Neustadt, B.R.1    Smith, E.M.2    Nechuta, T.3    Zhang, Y.Z.4
  • 16
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    • and refs. cited therein
    • See ref. l(a) and: (a) Boyce, R.; Li, G.; Nestler, H. P.; Suenaga, T.; Still, W. C. J. Am. Chem. Soc. 1994, 116, 7955; (b) Cheng, Y. A.; Suenaga, T.; Still, W. C. J. Am. Chem. Soc. 1996, 118, 1813; (c) Wess, G.; Bock, K.; Kleine, H.; Kurz, M.; Guba, W.; Hemmerle, H.; Lopez-Calle, E.; Baringhaus, K. H.; Glombik, H.; Enhsen, A.; Kramer, W. Angew. Chem., Int. Ed. Engl. 1996, 35, 2222; (d) Kasal, A.; Kohout, L.; Lebl, M. Coll. Czech. Chem. Comm. 1995, 60, 2147; (e) Broderick, S.; Davis, A. F.; Williams, R. P. Tetrahedron Lett. 1998, 39, 6083; (f) Kocis, P.; Issakova, O.; Sepetov, N. F.; Lebl, M. Tetrahedron Lett. 1995, 36, 6623; (g) Neustadt, B. R.; Smith, E. M.; Nechuta, T.; Zhang, Y. Z. Tetrahedron Lett. 1998, 39, 5317 (and refs. cited therein); (h) Wunberg, T.; Kallus, C.; Opatz, T.; Henke, S.; Schmidt, W.; Kunz, H. Angew. Chem., Int. Ed. Engl. 1998, 37, 2503 (and refs. cited therein); (i) Pryor, K. E.; Shipps, G. W.; Skyler, D. A.; Rebek, J. Tetrahedron 1998, 54, 4107 (and refs. cited therein); (j) Mink, D.; Mecozzi, S.; Rebek, J. Tetrahedron Lett. 1998, 39, 5709.
    • (1998) Angew. Chem., Int. Ed. Engl. , vol.37 , pp. 2503
    • Wunberg, T.1    Kallus, C.2    Opatz, T.3    Henke, S.4    Schmidt, W.5    Kunz, H.6
  • 17
    • 0032537036 scopus 로고    scopus 로고
    • and refs. cited therein
    • See ref. l(a) and: (a) Boyce, R.; Li, G.; Nestler, H. P.; Suenaga, T.; Still, W. C. J. Am. Chem. Soc. 1994, 116, 7955; (b) Cheng, Y. A.; Suenaga, T.; Still, W. C. J. Am. Chem. Soc. 1996, 118, 1813; (c) Wess, G.; Bock, K.; Kleine, H.; Kurz, M.; Guba, W.; Hemmerle, H.; Lopez-Calle, E.; Baringhaus, K. H.; Glombik, H.; Enhsen, A.; Kramer, W. Angew. Chem., Int. Ed. Engl. 1996, 35, 2222; (d) Kasal, A.; Kohout, L.; Lebl, M. Coll. Czech. Chem. Comm. 1995, 60, 2147; (e) Broderick, S.; Davis, A. F.; Williams, R. P. Tetrahedron Lett. 1998, 39, 6083; (f) Kocis, P.; Issakova, O.; Sepetov, N. F.; Lebl, M. Tetrahedron Lett. 1995, 36, 6623; (g) Neustadt, B. R.; Smith, E. M.; Nechuta, T.; Zhang, Y. Z. Tetrahedron Lett. 1998, 39, 5317 (and refs. cited therein); (h) Wunberg, T.; Kallus, C.; Opatz, T.; Henke, S.; Schmidt, W.; Kunz, H. Angew. Chem., Int. Ed. Engl. 1998, 37, 2503 (and refs. cited therein); (i) Pryor, K. E.; Shipps, G. W.; Skyler, D. A.; Rebek, J. Tetrahedron 1998, 54, 4107 (and refs. cited therein); (j) Mink, D.; Mecozzi, S.; Rebek, J. Tetrahedron Lett. 1998, 39, 5709.
    • (1998) Tetrahedron , vol.54 , pp. 4107
    • Pryor, K.E.1    Shipps, G.W.2    Skyler, D.A.3    Rebek, J.4
  • 18
    • 0032491014 scopus 로고    scopus 로고
    • See ref. l(a) and: (a) Boyce, R.; Li, G.; Nestler, H. P.; Suenaga, T.; Still, W. C. J. Am. Chem. Soc. 1994, 116, 7955; (b) Cheng, Y. A.; Suenaga, T.; Still, W. C. J. Am. Chem. Soc. 1996, 118, 1813; (c) Wess, G.; Bock, K.; Kleine, H.; Kurz, M.; Guba, W.; Hemmerle, H.; Lopez-Calle, E.; Baringhaus, K. H.; Glombik, H.; Enhsen, A.; Kramer, W. Angew. Chem., Int. Ed. Engl. 1996, 35, 2222; (d) Kasal, A.; Kohout, L.; Lebl, M. Coll. Czech. Chem. Comm. 1995, 60, 2147; (e) Broderick, S.; Davis, A. F.; Williams, R. P. Tetrahedron Lett. 1998, 39, 6083; (f) Kocis, P.; Issakova, O.; Sepetov, N. F.; Lebl, M. Tetrahedron Lett. 1995, 36, 6623; (g) Neustadt, B. R.; Smith, E. M.; Nechuta, T.; Zhang, Y. Z. Tetrahedron Lett. 1998, 39, 5317 (and refs. cited therein); (h) Wunberg, T.; Kallus, C.; Opatz, T.; Henke, S.; Schmidt, W.; Kunz, H. Angew. Chem., Int. Ed. Engl. 1998, 37, 2503 (and refs. cited therein); (i) Pryor, K. E.; Shipps, G. W.; Skyler, D. A.; Rebek, J. Tetrahedron 1998, 54, 4107 (and refs. cited therein); (j) Mink, D.; Mecozzi, S.; Rebek, J. Tetrahedron Lett. 1998, 39, 5709.
    • (1998) Tetrahedron Lett. , vol.39 , pp. 5709
    • Mink, D.1    Mecozzi, S.2    Rebek, J.3
  • 19
    • 0013562737 scopus 로고    scopus 로고
    • note
    • The synthesis of a differentially-protected 7α,12ß-diamine from 1 is reported in ref. 4d. The stereochemical assignment at C12 may be thought uncertain in view of the present work, but if the original authors are correct this scaffold would present divergent functionality to a target receptor or substrate. Ref. 4e describes the conversion of 1 into the corresponding 3α,7α,12α-triamine, but does not establish differential protection of the amino groups.
  • 22
    • 0013563104 scopus 로고    scopus 로고
    • note
    • 3H in toluene, reducing the exposure of the NHBoc group to the acidic conditions.
  • 24
    • 0013593555 scopus 로고    scopus 로고
    • note
    • Acetate 7 was also prepared via a separate route employing azide 8 as an intermediate. (Formula presented)
  • 25
    • 0013617789 scopus 로고    scopus 로고
    • note
    • -3 in the final difference map.


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