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Volumn 64, Issue 12, 1999, Pages 4339-4343

Effects of propargylic substitution and annelation on the cycloaromatization of a Bicyclo[7.3.1] enediyne

Author keywords

[No Author keywords available]

Indexed keywords

CALICHEAMICIN; ESPERAMICIN;

EID: 0033546365     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo982231i     Document Type: Article
Times cited : (13)

References (40)
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    • For reviews of enediyne chemistry and biology, see: (a) Grissom, J. W.; Gunawardena, G. U.; Klingberg, D.; Huang, D. Tetrahedron 1996, 52, 6453. (b) Maier, M. E. Synlett 1995, 13. (c) Nicolaou, K. C.; Dai, W.-M. Angew. Chem., Int. Ed. Engl. 1991, 30, 1387. (d) Doyle, T. W., Borders, D. B., Eds. Enediyne Antibiotics as Antitumor Agents; Marcel-Dekker: New York, 1994.
    • (1996) Tetrahedron , vol.52 , pp. 6453
    • Grissom, J.W.1    Gunawardena, G.U.2    Klingberg, D.3    Huang, D.4
  • 6
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    • For reviews of enediyne chemistry and biology, see: (a) Grissom, J. W.; Gunawardena, G. U.; Klingberg, D.; Huang, D. Tetrahedron 1996, 52, 6453. (b) Maier, M. E. Synlett 1995, 13. (c) Nicolaou, K. C.; Dai, W.-M. Angew. Chem., Int. Ed. Engl. 1991, 30, 1387. (d) Doyle, T. W., Borders, D. B., Eds. Enediyne Antibiotics as Antitumor Agents; Marcel-Dekker: New York, 1994.
    • (1995) Synlett , pp. 13
    • Maier, M.E.1
  • 7
    • 0026045597 scopus 로고
    • For reviews of enediyne chemistry and biology, see: (a) Grissom, J. W.; Gunawardena, G. U.; Klingberg, D.; Huang, D. Tetrahedron 1996, 52, 6453. (b) Maier, M. E. Synlett 1995, 13. (c) Nicolaou, K. C.; Dai, W.-M. Angew. Chem., Int. Ed. Engl. 1991, 30, 1387. (d) Doyle, T. W., Borders, D. B., Eds. Enediyne Antibiotics as Antitumor Agents; Marcel-Dekker: New York, 1994.
    • (1991) Angew. Chem., Int. Ed. Engl. , vol.30 , pp. 1387
    • Nicolaou, K.C.1    Dai, W.-M.2
  • 8
    • 0030005845 scopus 로고    scopus 로고
    • Marcel-Dekker: New York
    • For reviews of enediyne chemistry and biology, see: (a) Grissom, J. W.; Gunawardena, G. U.; Klingberg, D.; Huang, D. Tetrahedron 1996, 52, 6453. (b) Maier, M. E. Synlett 1995, 13. (c) Nicolaou, K. C.; Dai, W.-M. Angew. Chem., Int. Ed. Engl. 1991, 30, 1387. (d) Doyle, T. W., Borders, D. B., Eds. Enediyne Antibiotics as Antitumor Agents; Marcel-Dekker: New York, 1994.
    • (1994) Enediyne Antibiotics as Antitumor Agents
    • Doyle, T.W.1    Borders, D.B.2
  • 16
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    • For syntheses of calicheamicinone and calicheamicin analogues, see ref 2; for recent reports, see: (a) Clive, D. L. J.; Bo, Y.; Tao, Y.; Daigneault, S.; Wu, Y.-J.; Meignan, G. J. Am. Chem. Soc. 1996, 118, 4904. (b) Churcher, I.; Hallett, D.; Magnus, P. Ibid. 1998, 120, 3518.
    • (1996) J. Am. Chem. Soc. , vol.118 , pp. 4904
    • Clive, D.L.J.1    Bo, Y.2    Tao, Y.3    Daigneault, S.4    Wu, Y.-J.5    Meignan, G.6
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    • For syntheses of calicheamicinone and calicheamicin analogues, see ref 2; for recent reports, see: (a) Clive, D. L. J.; Bo, Y.; Tao, Y.; Daigneault, S.; Wu, Y.-J.; Meignan, G. J. Am. Chem. Soc. 1996, 118, 4904. (b) Churcher, I.; Hallett, D.; Magnus, P. Ibid. 1998, 120, 3518.
    • (1998) J. Am. Chem. Soc. , vol.120 , pp. 3518
    • Churcher, I.1    Hallett, D.2    Magnus, P.3
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    • -1; see: (a) Magnus, P.; Fortt, S.; Pitterna, T.; Snyder, J. P. J. Am. Chem. Soc. 1990, 112, 4986. (b) Magnus, P.; Carter, P.; Elliott, J.; Lewis, R.; Harling, J.; Pitterna, T.; Bauta, W. E.; Fortt, S. Ibid. 1992, 114, 2544.
    • (1990) J. Am. Chem. Soc. , vol.112 , pp. 4986
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    • Enediyne 2 undergoes complete cycloaromatization at 20°C within 30 min; see ref 6
    • Enediyne 2 undergoes complete cycloaromatization at 20°C within 30 min; see ref 6.
  • 28
    • 33748243199 scopus 로고    scopus 로고
    • For a survey on methods for the closure of enediyne rings, see: Konig, B. Angew. Chem., Int. Ed. Engl. 1996, 35, 165.
    • (1996) Angew. Chem., Int. Ed. Engl. , vol.35 , pp. 165
    • Konig, B.1
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    • Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, Chapter 1.8 and references therein
    • For papers illustrating the use of cerium-derived nucleophiles, see: (a) Imamoto, T. In Comprehensive Organic Synthesis, Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 1, Chapter 1.8 and references therein. (b) Imamoto, T. Pure Appl. Chem. 1990, 62, 747. For comparison of the lithium and cerium ion-pair acidities of some terminal alkynes, see Gareyev, R.; Streitwieser, A. J. Org. Chem. 1996, 61, 1742.
    • (1991) Comprehensive Organic Synthesis , vol.1
    • Imamoto, T.1
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    • For papers illustrating the use of cerium-derived nucleophiles, see: (a) Imamoto, T. In Comprehensive Organic Synthesis, Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 1, Chapter 1.8 and references therein. (b) Imamoto, T. Pure Appl. Chem. 1990, 62, 747. For comparison of the lithium and cerium ion-pair acidities of some terminal alkynes, see Gareyev, R.; Streitwieser, A. J. Org. Chem. 1996, 61, 1742.
    • (1990) Pure Appl. Chem. , vol.62 , pp. 747
    • Imamoto, T.1
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    • 0006687524 scopus 로고    scopus 로고
    • For papers illustrating the use of cerium-derived nucleophiles, see: (a) Imamoto, T. In Comprehensive Organic Synthesis, Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 1, Chapter 1.8 and references therein. (b) Imamoto, T. Pure Appl. Chem. 1990, 62, 747. For comparison of the lithium and cerium ion-pair acidities of some terminal alkynes, see Gareyev, R.; Streitwieser, A. J. Org. Chem. 1996, 61, 1742.
    • (1996) J. Org. Chem. , vol.61 , pp. 1742
    • Gareyev, R.1    Streitwieser, A.2
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    • Prepared by the condensation of dry acetylene gas into THF at -78°C followed by treatment with n-BuLi (see, Midland, M. M.; McLoughlin, J. I.; Werley, R. T. Org. Synth. 1989, 68, 14) and transmetalation with cerium chloride.
    • (1989) Org. Synth. , vol.68 , pp. 14
    • Midland, M.M.1    McLoughlin, J.I.2    Werley, R.T.3
  • 35
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    • Crystal data for 13 may be obtained from Cambridge Cryatallographic Data Centre; deposition CCDC 107106
    • Crystal data for 13 may be obtained from Cambridge Cryatallographic Data Centre; deposition CCDC 107106.
  • 39
    • 0344794339 scopus 로고    scopus 로고
    • note
    • 1H NMR spectra for the recovered materials were identical to those of the purified starting compounds 5 and 6.


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