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Volumn 33, Issue 6, 1996, Pages 1995-2005

Synthesis of new pyridine intermediates as precursors for the elaboration of streptonigrin analogues by the metalation-cross-coupling strategy

Author keywords

[No Author keywords available]

Indexed keywords

QUINOLINE DERIVATIVE; STREPTONIGRIN DERIVATIVE;

EID: 0030512291     PISSN: 0022152X     EISSN: None     Source Type: Journal    
DOI: 10.1002/jhet.5570330670     Document Type: Article
Times cited : (21)

References (30)
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    • For antitumor and anti HIV activity, see [1a] K. V. Rao and W. P. Cullen, Antibiot. Annu., 950 (1959) [1b] T. J. Bride, J. J. Oleson, and D. Woolf, Cancer. Res., 26, 727 (1966).
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    • Bride, T.J.1    Oleson, J.J.2    Woolf, D.3
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    • For total synthesis of streptonigrin, see [2a] F. Z. Basha, S. Hibino, D. Kim, W. E. Pye, T. T. Wu, and S. M. Weinreb, J. Am. Chem. Soc., 102, 3962 (1980) [2b] A. S. Kende, D. P. Lorah, and R. J. Boatman, J. Am. Chem. Soc., 103, 1271 (1981) [2c] D. L. Boger and J. S. Panek, J. Am. Chem. Soc., 107, 5745 (1985); for synthesis of streptonigrin analogues, see examples [2d] M. Cushman and J. J. Mathew, J. Org. Chem., 45, 4921 (1981) [2e] K. V. Rao and Hsien-Saw Kuo, J. Heterocyclic Chem., 16, 1241 (1979).
    • (1980) J. Am. Chem. Soc. , vol.102 , pp. 3962
    • Basha, F.Z.1    Hibino, S.2    Kim, D.3    Pye, W.E.4    Wu, T.T.5    Weinreb, S.M.6
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    • For total synthesis of streptonigrin, see [2a] F. Z. Basha, S. Hibino, D. Kim, W. E. Pye, T. T. Wu, and S. M. Weinreb, J. Am. Chem. Soc., 102, 3962 (1980) [2b] A. S. Kende, D. P. Lorah, and R. J. Boatman, J. Am. Chem. Soc., 103, 1271 (1981) [2c] D. L. Boger and J. S. Panek, J. Am. Chem. Soc., 107, 5745 (1985); for synthesis of streptonigrin analogues, see examples [2d] M. Cushman and J. J. Mathew, J. Org. Chem., 45, 4921 (1981) [2e] K. V. Rao and Hsien-Saw Kuo, J. Heterocyclic Chem., 16, 1241 (1979).
    • (1981) J. Am. Chem. Soc. , vol.103 , pp. 1271
    • Kende, A.S.1    Lorah, D.P.2    Boatman, R.J.3
  • 5
    • 0022398192 scopus 로고
    • For total synthesis of streptonigrin, see [2a] F. Z. Basha, S. Hibino, D. Kim, W. E. Pye, T. T. Wu, and S. M. Weinreb, J. Am. Chem. Soc., 102, 3962 (1980) [2b] A. S. Kende, D. P. Lorah, and R. J. Boatman, J. Am. Chem. Soc., 103, 1271 (1981) [2c] D. L. Boger and J. S. Panek, J. Am. Chem. Soc., 107, 5745 (1985); for synthesis of streptonigrin analogues, see examples [2d] M. Cushman and J. J. Mathew, J. Org. Chem., 45, 4921 (1981) [2e] K. V. Rao and Hsien-Saw Kuo, J. Heterocyclic Chem., 16, 1241 (1979).
    • (1985) J. Am. Chem. Soc. , vol.107 , pp. 5745
    • Boger, D.L.1    Panek, J.S.2
  • 6
    • 0019853633 scopus 로고
    • For total synthesis of streptonigrin, see [2a] F. Z. Basha, S. Hibino, D. Kim, W. E. Pye, T. T. Wu, and S. M. Weinreb, J. Am. Chem. Soc., 102, 3962 (1980) [2b] A. S. Kende, D. P. Lorah, and R. J. Boatman, J. Am. Chem. Soc., 103, 1271 (1981) [2c] D. L. Boger and J. S. Panek, J. Am. Chem. Soc., 107, 5745 (1985); for synthesis of streptonigrin analogues, see examples [2d] M. Cushman and J. J. Mathew, J. Org. Chem., 45, 4921 (1981) [2e] K. V. Rao and Hsien-Saw Kuo, J. Heterocyclic Chem., 16, 1241 (1979).
    • (1981) J. Org. Chem. , vol.45 , pp. 4921
    • Cushman, M.1    Mathew, J.J.2
  • 7
    • 0005196847 scopus 로고
    • For total synthesis of streptonigrin, see [2a] F. Z. Basha, S. Hibino, D. Kim, W. E. Pye, T. T. Wu, and S. M. Weinreb, J. Am. Chem. Soc., 102, 3962 (1980) [2b] A. S. Kende, D. P. Lorah, and R. J. Boatman, J. Am. Chem. Soc., 103, 1271 (1981) [2c] D. L. Boger and J. S. Panek, J. Am. Chem. Soc., 107, 5745 (1985); for synthesis of streptonigrin analogues, see examples [2d] M. Cushman and J. J. Mathew, J. Org. Chem., 45, 4921 (1981) [2e] K. V. Rao and Hsien-Saw Kuo, J. Heterocyclic Chem., 16, 1241 (1979).
    • (1979) J. Heterocyclic Chem. , vol.16 , pp. 1241
    • Rao, K.V.1    Kuo, H.-S.2
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    • See [3c] and [5]
    • See [3c] and [5];
  • 11
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    • see also [5] [3d] For others publications relating to streptonigrin, see: A. Godard, J. M. Fourquez, R. Tamion, F. Marsais, and G. Queguiner, Synlett., 235 (1994); A. Godard, P. Rocca, J. M. Fourquez, J. C. Rovera, F. Marsais, and G. Queguiner, Tetrahedron Letters, 34, 7919 (1993).
    • (1994) Synlett. , pp. 235
    • Godard, A.1    Fourquez, J.M.2    Tamion, R.3    Marsais, F.4    Queguiner, G.5
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    • K. V. Rao, Cancer. Chemother. Rep., 4 (part 2), 11 (1974); K. V. Rao, J. Heterocyclic Chem., 12, 725 (1975).
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    • Rao, K.V.1
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    • 0016764833 scopus 로고
    • K. V. Rao, Cancer. Chemother. Rep., 4 (part 2), 11 (1974); K. V. Rao, J. Heterocyclic Chem., 12, 725 (1975).
    • (1975) J. Heterocyclic Chem. , vol.12 , pp. 725
    • Rao, K.V.1
  • 18
    • 0026645975 scopus 로고
    • Typical procedures of picolines oxidation, see example [8a] selenium dioxide: W. Yuqiang, L. Mao-Chin, and A. C. Sartorelli, J. Med. Chem., 35, 3667 (1992) [8b] Benzaldehyde/zinc chloride: I. Mahadevan and M. Rasmussen, J. Heterocyclic Chem., 29, 359 (1992) [8c] Hydrogen Peroxide/acetic anhydride: S. Oae, S. Tamagaki, T. Negoro, and S. Kozuka, Tetrahedron, 26, 4051 (1970) [8d] NBS/carbon tetrachloride of potassium permanganate/water: T. Lihama, J.-M. Fu, M. Bourguignon, and V. Snieckus, Synthesis, 184 (1989) [8d] Iodine/DMSO: A. Markovac and B. E. Hackley, Jr., J. Org. Chem., 35, 841 (1970).
    • (1992) J. Med. Chem. , vol.35 , pp. 3667
    • Yuqiang, W.1    Mao-Chin, L.2    Sartorelli, A.C.3
  • 19
    • 84986469517 scopus 로고
    • Typical procedures of picolines oxidation, see example [8a] selenium dioxide: W. Yuqiang, L. Mao-Chin, and A. C. Sartorelli, J. Med. Chem., 35, 3667 (1992) [8b] Benzaldehyde/zinc chloride: I. Mahadevan and M. Rasmussen, J. Heterocyclic Chem., 29, 359 (1992) [8c] Hydrogen Peroxide/acetic anhydride: S. Oae, S. Tamagaki, T. Negoro, and S. Kozuka, Tetrahedron, 26, 4051 (1970) [8d] NBS/carbon tetrachloride of potassium permanganate/water: T. Lihama, J.-M. Fu, M. Bourguignon, and V. Snieckus, Synthesis, 184 (1989) [8d] Iodine/DMSO: A. Markovac and B. E. Hackley, Jr., J. Org. Chem., 35, 841 (1970).
    • (1992) J. Heterocyclic Chem. , vol.29 , pp. 359
    • Chloride, B.1    Mahadevan, I.2    Rasmussen, M.3
  • 20
    • 8044258817 scopus 로고
    • Typical procedures of picolines oxidation, see example [8a] selenium dioxide: W. Yuqiang, L. Mao-Chin, and A. C. Sartorelli, J. Med. Chem., 35, 3667 (1992) [8b] Benzaldehyde/zinc chloride: I. Mahadevan and M. Rasmussen, J. Heterocyclic Chem., 29, 359 (1992) [8c] Hydrogen Peroxide/acetic anhydride: S. Oae, S. Tamagaki, T. Negoro, and S. Kozuka, Tetrahedron, 26, 4051 (1970) [8d] NBS/carbon tetrachloride of potassium permanganate/water: T. Lihama, J.-M. Fu, M. Bourguignon, and V. Snieckus, Synthesis, 184 (1989) [8d] Iodine/DMSO: A. Markovac and B. E. Hackley, Jr., J. Org. Chem., 35, 841 (1970).
    • (1970) Tetrahedron , vol.26 , pp. 4051
    • Oae, S.1    Tamagaki, S.2    Negoro, T.3    Kozuka, S.4
  • 21
    • 0002613596 scopus 로고
    • Typical procedures of picolines oxidation, see example [8a] selenium dioxide: W. Yuqiang, L. Mao-Chin, and A. C. Sartorelli, J. Med. Chem., 35, 3667 (1992) [8b] Benzaldehyde/zinc chloride: I. Mahadevan and M. Rasmussen, J. Heterocyclic Chem., 29, 359 (1992) [8c] Hydrogen Peroxide/acetic anhydride: S. Oae, S. Tamagaki, T. Negoro, and S. Kozuka, Tetrahedron, 26, 4051 (1970) [8d] NBS/carbon tetrachloride of potassium permanganate/water: T. Lihama, J.-M. Fu, M. Bourguignon, and V. Snieckus, Synthesis, 184 (1989) [8d] Iodine/DMSO: A. Markovac and B. E. Hackley, Jr., J. Org. Chem., 35, 841 (1970).
    • (1989) Synthesis , pp. 184
    • Lihama, T.1    Fu, J.-M.2    Bourguignon, M.3    Snieckus, V.4
  • 22
    • 0038210873 scopus 로고
    • Typical procedures of picolines oxidation, see example [8a] selenium dioxide: W. Yuqiang, L. Mao-Chin, and A. C. Sartorelli, J. Med. Chem., 35, 3667 (1992) [8b] Benzaldehyde/zinc chloride: I. Mahadevan and M. Rasmussen, J. Heterocyclic Chem., 29, 359 (1992) [8c] Hydrogen Peroxide/acetic anhydride: S. Oae, S. Tamagaki, T. Negoro, and S. Kozuka, Tetrahedron, 26, 4051 (1970) [8d] NBS/carbon tetrachloride of potassium permanganate/water: T. Lihama, J.-M. Fu, M. Bourguignon, and V. Snieckus, Synthesis, 184 (1989) [8d] Iodine/DMSO: A. Markovac and B. E. Hackley, Jr., J. Org. Chem., 35, 841 (1970).
    • (1970) J. Org. Chem. , vol.35 , pp. 841
    • Markovac, A.1    Hackley Jr., B.E.2


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