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Volumn 3, Issue 9, 2001, Pages 1347-1349

Tandem cationic aza-Cope rearrangement-Mannich cyclization approach to the core structure of FR901483 via a bridgehead iminium ion

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOHEXANONE; CYCLOHEXANONE DERIVATIVE; FR 901483; IMMUNOSUPPRESSIVE AGENT; ION; ORGANOPHOSPHORUS COMPOUND;

EID: 0035799870     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol010029n     Document Type: Article
Times cited : (59)

References (27)
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    • (c) Snider, B. B.; Lin, H. J. Am. Chem. Soc. 1999, 121, 7778. For the total synthesis of (±)-FR901483, see:
    • (1999) J. Am. Chem. Soc. , vol.121 , pp. 7778
    • Snider, B.B.1    Lin, H.2
  • 13
    • 0032915617 scopus 로고    scopus 로고
    • Yamazaki, N.; Ito, T.; Kibayashi, C. Synlett 1999, 37. For references concerning bridgehead imines, see: Braje, W. M.; Wartchow, R.; Hoffman, M. R. Angew. Chem., Int. Ed. 1999, 38, 2540. Wayne, G. S.; Snyder, G. J. J. Am. Chem. Soc. 1993, 115, 9860. Radziszewski, J. G.; Downing, J. W.; Wentrup, C.; Kaszynski, P.; Jawdosiuk, M.; Kovacic, P.; Michl, J. J. Am. Chem. Soc. 1985, 107, 2799. Sheridan, R. S.; Ganzer, G. A. J. Am. Chem. Soc. 1983, 105, 6158. Toda, M.; Hirata, Y. Yamamura, S. J. Chem. Soc., Chem. Commun. 1970, 1597.
    • (1999) Synlett , pp. 37
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  • 14
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    • Yamazaki, N.; Ito, T.; Kibayashi, C. Synlett 1999, 37. For references concerning bridgehead imines, see: Braje, W. M.; Wartchow, R.; Hoffman, M. R. Angew. Chem., Int. Ed. 1999, 38, 2540. Wayne, G. S.; Snyder, G. J. J. Am. Chem. Soc. 1993, 115, 9860. Radziszewski, J. G.; Downing, J. W.; Wentrup, C.; Kaszynski, P.; Jawdosiuk, M.; Kovacic, P.; Michl, J. J. Am. Chem. Soc. 1985, 107, 2799. Sheridan, R. S.; Ganzer, G. A. J. Am. Chem. Soc. 1983, 105, 6158. Toda, M.; Hirata, Y. Yamamura, S. J. Chem. Soc., Chem. Commun. 1970, 1597.
    • (1999) Angew. Chem., Int. Ed. , vol.38 , pp. 2540
    • Braje, W.M.1    Wartchow, R.2    Hoffman, M.R.3
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    • Yamazaki, N.; Ito, T.; Kibayashi, C. Synlett 1999, 37. For references concerning bridgehead imines, see: Braje, W. M.; Wartchow, R.; Hoffman, M. R. Angew. Chem., Int. Ed. 1999, 38, 2540. Wayne, G. S.; Snyder, G. J. J. Am. Chem. Soc. 1993, 115, 9860. Radziszewski, J. G.; Downing, J. W.; Wentrup, C.; Kaszynski, P.; Jawdosiuk, M.; Kovacic, P.; Michl, J. J. Am. Chem. Soc. 1985, 107, 2799. Sheridan, R. S.; Ganzer, G. A. J. Am. Chem. Soc. 1983, 105, 6158. Toda, M.; Hirata, Y. Yamamura, S. J. Chem. Soc., Chem. Commun. 1970, 1597.
    • (1993) J. Am. Chem. Soc. , vol.115 , pp. 9860
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    • Yamazaki, N.; Ito, T.; Kibayashi, C. Synlett 1999, 37. For references concerning bridgehead imines, see: Braje, W. M.; Wartchow, R.; Hoffman, M. R. Angew. Chem., Int. Ed. 1999, 38, 2540. Wayne, G. S.; Snyder, G. J. J. Am. Chem. Soc. 1993, 115, 9860. Radziszewski, J. G.; Downing, J. W.; Wentrup, C.; Kaszynski, P.; Jawdosiuk, M.; Kovacic, P.; Michl, J. J. Am. Chem. Soc. 1985, 107, 2799. Sheridan, R. S.; Ganzer, G. A. J. Am. Chem. Soc. 1983, 105, 6158. Toda, M.; Hirata, Y. Yamamura, S. J. Chem. Soc., Chem. Commun. 1970, 1597.
    • (1985) J. Am. Chem. Soc. , vol.107 , pp. 2799
    • Radziszewski, J.G.1    Downing, J.W.2    Wentrup, C.3    Kaszynski, P.4    Jawdosiuk, M.5    Kovacic, P.6    Michl, J.7
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    • Yamazaki, N.; Ito, T.; Kibayashi, C. Synlett 1999, 37. For references concerning bridgehead imines, see: Braje, W. M.; Wartchow, R.; Hoffman, M. R. Angew. Chem., Int. Ed. 1999, 38, 2540. Wayne, G. S.; Snyder, G. J. J. Am. Chem. Soc. 1993, 115, 9860. Radziszewski, J. G.; Downing, J. W.; Wentrup, C.; Kaszynski, P.; Jawdosiuk, M.; Kovacic, P.; Michl, J. J. Am. Chem. Soc. 1985, 107, 2799. Sheridan, R. S.; Ganzer, G. A. J. Am. Chem. Soc. 1983, 105, 6158. Toda, M.; Hirata, Y. Yamamura, S. J. Chem. Soc., Chem. Commun. 1970, 1597.
    • (1983) J. Am. Chem. Soc. , vol.105 , pp. 6158
    • Sheridan, R.S.1    Ganzer, G.A.2
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    • Yamazaki, N.; Ito, T.; Kibayashi, C. Synlett 1999, 37. For references concerning bridgehead imines, see: Braje, W. M.; Wartchow, R.; Hoffman, M. R. Angew. Chem., Int. Ed. 1999, 38, 2540. Wayne, G. S.; Snyder, G. J. J. Am. Chem. Soc. 1993, 115, 9860. Radziszewski, J. G.; Downing, J. W.; Wentrup, C.; Kaszynski, P.; Jawdosiuk, M.; Kovacic, P.; Michl, J. J. Am. Chem. Soc. 1985, 107, 2799. Sheridan, R. S.; Ganzer, G. A. J. Am. Chem. Soc. 1983, 105, 6158. Toda, M.; Hirata, Y. Yamamura, S. J. Chem. Soc., Chem. Commun. 1970, 1597.
    • (1970) J. Chem. Soc., Chem. Commun. , pp. 1597
    • Toda, M.1    Hirata, Y.2    Yamamura, S.3
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    • references therein
    • The choice of butanediol as the reagent for protection is based on the facile removal of the resulting dioxepane ketal. Snider, B. B.; Lin, H. Org. Lett. 2000, 2, 643 and references therein.
    • (2000) Org. Lett. , vol.2 , pp. 643
    • Snider, B.B.1    Lin, H.2
  • 27
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    • note
    • 3, and t-BuOH to afford the desired Boc protected amine in 21% yield. While the yield is low, this reaction sequence provides support for the successful application of this approach to FR901483 and will be optimized.


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