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Volumn 132, Issue 3, 2010, Pages 1151-1158

Total synthesis of the N,C-coupled naphthylisoquinoline alkaloids ancistrocladinium A and B and related analogues

Author keywords

[No Author keywords available]

Indexed keywords

CONFIGURATIONALLY; DIASTEREOMERS; IMINIUM; IN-VITRO; PROTECTING GROUP; SHORT SEQUENCES; STRUCTURAL ANALOGUE; STRUCTURE ACTIVITY RELATIONSHIPS; TOTAL SYNTHESIS;

EID: 76149106183     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9097687     Document Type: Article
Times cited : (57)

References (70)
  • 1
    • 77957089074 scopus 로고
    • Cordell, G. A, Ed, Academic Press: San Diego, CA
    • Bringmann, G.; Pokorny, F. In The Alkaloids; Cordell, G. A., Ed.; Academic Press: San Diego, CA, 1995; pp 127-171.
    • (1995) The Alkaloids , pp. 127-171
    • Bringmann, G.1    Pokorny, F.2
  • 12
    • 76149103528 scopus 로고    scopus 로고
    • Bringmann, G.; Gulder, T.; Hentschel, U.; Meyer, F.; Moll, H.; Morschhäuser, J.; Ponte-Sucre De Vanegas, A.; Ziebuhr, W.; Stich, A.; Brun, R.; Müller, W. E. G.; Mudogo, V. Biofilm-Inhibiting Effect and Anti-Infective Activity of N,C-Linked Arylisoquinolines and the Use Thereof; PCT/EP2007/008440, 2007.
    • Bringmann, G.; Gulder, T.; Hentschel, U.; Meyer, F.; Moll, H.; Morschhäuser, J.; Ponte-Sucre De Vanegas, A.; Ziebuhr, W.; Stich, A.; Brun, R.; Müller, W. E. G.; Mudogo, V. Biofilm-Inhibiting Effect and Anti-Infective Activity of N,C-Linked Arylisoquinolines and the Use Thereof; PCT/EP2007/008440, 2007.
  • 28
    • 76149105135 scopus 로고    scopus 로고
    • Like for C,C-coupled analogues,70 a separate formation of the isoquinoline and naphthalene portion is assumed for the biosynthetic formation of 3 (as also for 2 and 4), followed by a phenol-oxidative cross coupling.
    • Like for C,C-coupled analogues,70 a separate formation of the isoquinoline and naphthalene portion is assumed for the biosynthetic formation of 3 (as also for 2 and 4), followed by a phenol-oxidative cross coupling.
  • 29
    • 0034801426 scopus 로고    scopus 로고
    • For a successful biomimetic cross coupling to give N,C-coupled dimers in the field of carbazole alkaloids, see: Bringmann, G.; Tasler, S.; Endress, H.; Kraus, J.; Messer, K.; Wohlfahrt, M.; Lobin, W. J. Am. Chem. Soc. 2001, 123, 2703.
    • For a successful biomimetic cross coupling to give N,C-coupled dimers in the field of carbazole alkaloids, see: Bringmann, G.; Tasler, S.; Endress, H.; Kraus, J.; Messer, K.; Wohlfahrt, M.; Lobin, W. J. Am. Chem. Soc. 2001, 123, 2703.
  • 41
    • 0003463148 scopus 로고    scopus 로고
    • Greene, T. W, Wuts, P. G. M, Eds, Wiley & Sons: New York
    • Protective Groups in Organic Synthesis; Greene, T. W., Wuts, P. G. M., Eds.; Wiley & Sons: New York, 1999.
    • (1999) Protective Groups in Organic Synthesis
  • 47
    • 76149106464 scopus 로고    scopus 로고
    • 33,34 the reaction time for generating the Grignard reagent was reduced from 12 to 2.5 h.
    • 33,34 the reaction time for generating the Grignard reagent was reduced from 12 to 2.5 h.
  • 51
    • 48549089345 scopus 로고    scopus 로고
    • For further, more recent Buchwald-Hartwig aminations on likewise electron-rich substrates, see: Organ, M. G.; Abdel-Hadi, M.; Avola, S.; Dubovyk, I.; Hadei, N.; Kantchev, E. A. B.; O'Brien, C. J.; Sayah, M.; Valente, C. Chem.-Eur. J. 2008, 14, 2443. Saelinger, D.; Brueckner, R. Synlett 2009, 109.
    • For further, more recent Buchwald-Hartwig aminations on likewise electron-rich substrates, see: Organ, M. G.; Abdel-Hadi, M.; Avola, S.; Dubovyk, I.; Hadei, N.; Kantchev, E. A. B.; O'Brien, C. J.; Sayah, M.; Valente, C. Chem.-Eur. J. 2008, 14, 2443. Saelinger, D.; Brueckner, R. Synlett 2009, 109.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.