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Volumn 43, Issue 41, 2002, Pages 7323-7327

Syntheses of brostallicin starting from distamycin A

Author keywords

Brostallicin; Curtius rearrangement; Diphenyl phosphorazidate; Distamycin A; Minor groove binders

Indexed keywords

AMIDE; ANTINEOPLASTIC AGENT; BROSTALLICIN; DISTAMYCIN A; POLYMER; UNCLASSIFIED DRUG;

EID: 0037037839     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(02)01733-1     Document Type: Article
Times cited : (12)

References (49)
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    • 0033591178 scopus 로고    scopus 로고
    • For some recent applications see also: (a) Magnus, P.; Westwood, N.; Spyvee, M.; Frost, C.; Linnane, P.; Tavares, F.; Lynch, V. Tetrahedron 1999, 55, 6435-6452; (b) Oscarsson, K.; Classon, B.; Kvarnström, I.; Hallberg, A.; Samuelsson, B. Can. J. Chem. 2000, 78, 829-837; (c) Evans, D. A.; Katz, J. L.; Peterson, G. S.; Hintermann, T. J. Am. Chem. Soc. 2001, 123, 12411-12413.
    • (1999) Tetrahedron , vol.55 , pp. 6435-6452
    • Magnus, P.1    Westwood, N.2    Spyvee, M.3    Frost, C.4    Linnane, P.5    Tavares, F.6    Lynch, V.7
  • 20
    • 0033846835 scopus 로고    scopus 로고
    • For some recent applications see also: (a) Magnus, P.; Westwood, N.; Spyvee, M.; Frost, C.; Linnane, P.; Tavares, F.; Lynch, V. Tetrahedron 1999, 55, 6435-6452; (b) Oscarsson, K.; Classon, B.; Kvarnström, I.; Hallberg, A.; Samuelsson, B. Can. J. Chem. 2000, 78, 829-837; (c) Evans, D. A.; Katz, J. L.; Peterson, G. S.; Hintermann, T. J. Am. Chem. Soc. 2001, 123, 12411-12413.
    • (2000) Can. J. Chem. , vol.78 , pp. 829-837
    • Oscarsson, K.1    Classon, B.2    Kvarnström, I.3    Hallberg, A.4    Samuelsson, B.5
  • 21
    • 0035852020 scopus 로고    scopus 로고
    • For some recent applications see also: (a) Magnus, P.; Westwood, N.; Spyvee, M.; Frost, C.; Linnane, P.; Tavares, F.; Lynch, V. Tetrahedron 1999, 55, 6435-6452; (b) Oscarsson, K.; Classon, B.; Kvarnström, I.; Hallberg, A.; Samuelsson, B. Can. J. Chem. 2000, 78, 829-837; (c) Evans, D. A.; Katz, J. L.; Peterson, G. S.; Hintermann, T. J. Am. Chem. Soc. 2001, 123, 12411-12413.
    • (2001) J. Am. Chem. Soc. , vol.123 , pp. 12411-12413
    • Evans, D.A.1    Katz, J.L.2    Peterson, G.S.3    Hintermann, T.4
  • 22
    • 84889136287 scopus 로고    scopus 로고
    • 1H NMR and MS spectra determinations were consistent with extensive nitrosation of the pyrrolic rings.
    • 1H NMR and MS spectra determinations were consistent with extensive nitrosation of the pyrrolic rings.
  • 24
    • 84889166836 scopus 로고    scopus 로고
    • -1, available from Sigma-Aldrich Cat. No. 35,988-2.
    • -1, available from Sigma-Aldrich Cat. No. 35,988-2.
  • 26
    • 84889112870 scopus 로고    scopus 로고
    • note
    • The reaction seems to start selectively in favor of intermediate 6 but when forced to completion non-selective paths take over.
  • 28
    • 0035804384 scopus 로고    scopus 로고
    • For recent advances in the field of polymer-supported reagents see (a) Ley, S. V.; Baxendale, I. R.; Bream, R. N.; Jackson, P. S.; Leach, A. G.; Longbottom, D. A.; Nesi, M.; Scott, J. S.; Storer, R. I.; Taylor, S. J. J. Chem. Soc., Perkin Trans. 1 2000, 23, 3815-4195; (b) Kirschning, A.; Monenschein, H.; Wittenberg, R. Angew. Chem., Int. Ed. 2001, 40, 650-679.
    • (2001) Angew. Chem., Int. Ed. , vol.40 , pp. 650-679
    • Kirschning, A.1    Monenschein, H.2    Wittenberg, R.3
  • 30
    • 84889156065 scopus 로고    scopus 로고
    • 2O was necessary in order to drive the reaction to completion.
    • 2O was necessary in order to drive the reaction to completion.
  • 31
    • 84889156448 scopus 로고    scopus 로고
    • 6) δ: 9.97 (s, 1H), 9.89 (s, 1H), 9.25 (s, 1H), 7.49 (d, J=1.8 Hz, 1H), 7.20 (d, J=1.8 Hz, 1H), 7.06 (d, J=1.8 Hz, 1H), 6.99 (d, J=1.8 Hz, 1H), 6.85 (d, J=1.8 Hz, 1H), 6.65 (d, J=1.8 Hz, 1H), 3.87 (s, 3H), 3.83 (s, 3H), 3.72 (s, 3H), 3.83 (m, 2H), 2.45 (t, J=6.2 Hz, 2H), 1.48 (s, 9H), 1.27 (s, 9H).
    • 6) δ: 9.97 (s, 1H), 9.89 (s, 1H), 9.25 (s, 1H), 7.49 (d, J=1.8 Hz, 1H), 7.20 (d, J=1.8 Hz, 1H), 7.06 (d, J=1.8 Hz, 1H), 6.99 (d, J=1.8 Hz, 1H), 6.85 (d, J=1.8 Hz, 1H), 6.65 (d, J=1.8 Hz, 1H), 3.87 (s, 3H), 3.83 (s, 3H), 3.72 (s, 3H), 3.83 (m, 2H), 2.45 (t, J=6.2 Hz, 2H), 1.48 (s, 9H), 1.27 (s, 9H).
  • 32
    • 84889135614 scopus 로고    scopus 로고
    • The yield of the hydrolysis was not optimized.
    • The yield of the hydrolysis was not optimized.
  • 34
    • 84889129592 scopus 로고    scopus 로고
    • note
    • 3N (4 equiv.) were reacted in DMF at 25-60°C. After several hours only starting material 6 was present.
  • 44
    • 84889127570 scopus 로고    scopus 로고
    • 6) δ: 9.87 (s, 1H), 9.83 (s, 1H), 9.05 (s, 1H), 7.50 (bs, 1H), 7.35 (d, J=1.7 Hz, 1H), 7.19 (d, J=1.7 Hz, 1H), 7.03 (d, J=1.7 Hz, 1H), 6.87 (bs, 1H), 6.81 (bs, 1H), 6.72 (d, J=1.7 Hz, 1H), 3.85-3.80 (m, 2H), 3.82 (s, 3H), 3.79 (s, 3H), 3.70 (s, 3H), 3.32-3.37 (m, 2H), 1.44 (s, 9H).
    • 6) δ: 9.87 (s, 1H), 9.83 (s, 1H), 9.05 (s, 1H), 7.50 (bs, 1H), 7.35 (d, J=1.7 Hz, 1H), 7.19 (d, J=1.7 Hz, 1H), 7.03 (d, J=1.7 Hz, 1H), 6.87 (bs, 1H), 6.81 (bs, 1H), 6.72 (d, J=1.7 Hz, 1H), 3.85-3.80 (m, 2H), 3.82 (s, 3H), 3.79 (s, 3H), 3.70 (s, 3H), 3.32-3.37 (m, 2H), 1.44 (s, 9H).
  • 45
    • 84889108174 scopus 로고    scopus 로고
    • tert-BuOH and MeOH have been tried.
    • tert-BuOH and MeOH have been tried.
  • 48
    • 84889141688 scopus 로고    scopus 로고
    • 6) δ: 9.85 (s, 1H), 9.82 (s, 1H), 9.05 (s, 1H), 8.01 (t, J=5.6 Hz, 1H), 7.19 (d, J=1.7 Hz, 1H), 7.16 (d, J=1.7 Hz, 1H), 7.02 (d, J=1.7 Hz, 1H), 6.89 (d, J=1.7 Hz, 1H), 6.87 (bs, 1H), 6.82 (bs, 1H), 3.82 (s, 3H), 3.79 (s, 3H), 3.78 (s, 3H), 3.26-3.20 (m, 2H), 2.74 (t, J=5.6 Hz, 1H).
    • 6) δ: 9.85 (s, 1H), 9.82 (s, 1H), 9.05 (s, 1H), 8.01 (t, J=5.6 Hz, 1H), 7.19 (d, J=1.7 Hz, 1H), 7.16 (d, J=1.7 Hz, 1H), 7.02 (d, J=1.7 Hz, 1H), 6.89 (d, J=1.7 Hz, 1H), 6.87 (bs, 1H), 6.82 (bs, 1H), 3.82 (s, 3H), 3.79 (s, 3H), 3.78 (s, 3H), 3.26-3.20 (m, 2H), 2.74 (t, J=5.6 Hz, 1H).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.