메뉴 건너뛰기




Volumn 2, Issue 2, 2002, Pages 113-126

Biarylic biscarbazole alkaloids: Occurrence, stereochemistry, synthesis, and bioactivity

Author keywords

Atroposelective synthesis; Biaryl coupling; Bioactivities; Biscarbazole alkaloids; Murraya

Indexed keywords

ALKALOID; DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS; LACTONE;

EID: 0036368894     PISSN: 15278999     EISSN: 15280691     Source Type: Journal    
DOI: 10.1002/tcr.10014     Document Type: Article
Times cited : (34)

References (76)
  • 1
    • 33746540525 scopus 로고    scopus 로고
    • note
    • The terms dimer and dimerization are used in this paper for reasons of simplicity; correctly speaking, these biaryls are didehydrodimers of the corresponding aromatic portions. Mind that in this paper, the numbering system for dimeric carbazoles has been set identically to that of the monomers, independent of the coupling site.
  • 2
    • 0035901346 scopus 로고    scopus 로고
    • For a synthesis of methylene-bridged binary carbazole alkaloids, see Bringmann, G.; Taster, S. Tetrahedron 2001, 57, 2337.
    • (2001) Tetrahedron , vol.57 , pp. 2337
    • Bringmann, G.1    Taster, S.2
  • 3
    • 77957036993 scopus 로고
    • Brossi, A., Ed.; Academic Press: New York
    • Chakraborty, D.P. In The Alkaloids, Vol. 44; Brossi, A., Ed.; Academic Press: New York, 1993; p. 257;
    • (1993) The Alkaloids , vol.44 , pp. 257
    • Chakraborty, D.P.1
  • 4
    • 0001524130 scopus 로고
    • Herz, W.; Grisebach, H.; Kirby, G.W.; Tamm, C., Eds. Springer: Wien
    • Bhattacharyya, P.; Chakraborty, D.P. In Prog Chem Org Nat Prod 52; Herz, W.; Grisebach, H.; Kirby, G.W.; Tamm, C., Eds. Springer: Wien, 1987; p. 159;
    • (1987) Prog Chem Org Nat Prod , vol.52 , pp. 159
    • Bhattacharyya, P.1    Chakraborty, D.P.2
  • 5
    • 0025999191 scopus 로고
    • Herz, W.; Kirby, G.W.; Steglich, W.; Tamm, C., Eds.; Springer: Wien
    • Chakraborty, D.P.; Roy, S. In Prog Chem Org Nat Prod 57; Herz, W.; Kirby, G.W.; Steglich, W.; Tamm, C., Eds.; Springer: Wien, 1991; p. 71.
    • (1991) Prog Chem Org Nat Prod , vol.57 , pp. 71
    • Chakraborty, D.P.1    Roy, S.2
  • 10
    • 0000297657 scopus 로고    scopus 로고
    • Scolastico, C.; Nicotra, F., Eds.; Kluwer Academic/Plenum Publishers: New York
    • Bringmann, G.; Tasler, S. In Current Trends in Organic Synthesis; Scolastico, C.; Nicotra, F., Eds.; Kluwer Academic/Plenum Publishers: New York, 1999, p. 105;
    • (1999) Current Trends in Organic Synthesis , pp. 105
    • Bringmann, G.1    Tasler, S.2
  • 13
    • 77957086242 scopus 로고
    • Manske, R.H.F., Ed.; Academic Press: New York
    • Kapil, R.S. In The Alkaloids, Vol. XIII; Manske, R.H.F., Ed.; Academic Press: New York, 1971; p. 273;
    • (1971) The Alkaloids , vol.13 , pp. 273
    • Kapil, R.S.1
  • 14
    • 0017378646 scopus 로고
    • Herz, W.; Grisebach, H.; Kirby, G.W., Eds.; Springer: Wien
    • Chakraborty, D.P. In Prog Chem Org Nat Prod 34; Herz, W.; Grisebach, H.; Kirby, G.W., Eds.; Springer: Wien, 1977; p. 299.
    • (1977) Prog Chem Org Nat Prod , vol.34 , pp. 299
    • Chakraborty, D.P.1
  • 21
    • 0001673644 scopus 로고
    • For C,N-bonded biarylic natural products other than biscarbazoles, see Norton, R.S.; Wells, R.J. J Am Chem Soc 1982, 104, 3628;
    • (1982) J Am Chem Soc , vol.104 , pp. 3628
    • Norton, R.S.1    Wells, R.J.2
  • 24
    • 0000750794 scopus 로고    scopus 로고
    • Schreier, P.; Herderich, M.; Humpf, H.U.; Schwab, W., Eds.; Vieweg: Braunschweig/Wiesbaden
    • Bringmann, G.; Busemann, S. In Natural Product Analysis; Schreier, P.; Herderich, M.; Humpf, H.U.; Schwab, W., Eds.; Vieweg: Braunschweig/Wiesbaden, 1998; p. 195;
    • (1998) Natural Product Analysis , pp. 195
    • Bringmann, G.1    Busemann, S.2
  • 27
    • 33746509691 scopus 로고    scopus 로고
    • note
    • The only exceptions to these substitution patterns are murrastifoline-A (12) and B (13).
  • 33
    • 0001659326 scopus 로고
    • Trost, B.M.; Fleming, I., Eds.; Pergamon Press: Oxford
    • Knight, D.W. In Comprehensive Organic Synthesis; Trost, B.M.; Fleming, I., Eds.; Pergamon Press: Oxford, 1991; p. 449.
    • (1991) Comprehensive Organic Synthesis , pp. 449
    • Knight, D.W.1
  • 36
    • 37049146966 scopus 로고
    • 4, or chromic acid have been known for more than 80 years, giving rise to a variety of N,N-, C,N-, and C,C-bonded bis-, ter-, and tetracarbazoles. Such reactions, however, were never performed on monomeric carbazole alkaloids and were not meant to afford dimeric natural products, therefore not leading to any of the 14 biscarbazole alkaloids known to date; see i.a.: Perkin, W.H.; Tucker, S.H. J Chem Soc 1921, 119, 216;
    • (1921) J Chem Soc , vol.119 , pp. 216
    • Perkin, W.H.1    Tucker, S.H.2
  • 40
    • 85042930885 scopus 로고
    • For an earlier report on an oxidatively dimerized side product (4,4′-dibromo-8,8′-biscarbazole) resulting from an AlCl3 mediated trans-tert-burylation of unnatural 4-bromo-2,7-di-tert-butylcarbazole to benzene, see Tashiro, M.; Yamato, T. Kenkyu Hokoku-Asahi Garasu Kogyo Gijutsu Shoreikai 1980, 36, 93;
    • (1980) Kenkyu Hokoku-Asahi Garasu Kogyo Gijutsu Shoreikai , vol.36 , pp. 93
    • Tashiro, M.1    Yamato, T.2
  • 49
    • 0034622898 scopus 로고    scopus 로고
    • note that the axial configuration of 1a, 2a, and 3a in Scheme 4 in this publication is drawn as (P) but described as (M) in the text
    • Lin, G.; Zhang, A. Tetrahedron 2000, 56, 7163; note that the axial configuration of 1a, 2a, and 3a in Scheme 4 in this publication is drawn as (P) but described as (M) in the text.
    • (2000) Tetrahedron , vol.56 , pp. 7163
    • Lin, G.1    Zhang, A.2
  • 73
    • 33746478565 scopus 로고    scopus 로고
    • Bringmann, G.; Tasler, S.; Brun, R.; Lohse, M. J. Unpublished results
    • Bringmann, G.; Tasler, S.; Brun, R.; Lohse, M. J. Unpublished results.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.