메뉴 건너뛰기




Volumn 37, Issue 9, 1996, Pages 1509-1512

Synthesis of 6-chloro-1,3,4,5-tetrahydro-7,8-dimethoxy-1-methylpyrrolo[4,3,2-de]quinoline from a quinoline; formal total syntheses of batzelline C, isobatzelline C, discorhabdin C and makaluvamine D

Author keywords

[No Author keywords available]

Indexed keywords

BATZELLINE C; DISCORHABDIN C; ISOBATZELLINE C; MAKALUVAMINE D; PYRROLO[4,3,2 DE]QUINOLINE DERIVATIVE; QUINOLINE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 0029925290     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00051-2     Document Type: Article
Times cited : (28)

References (48)
  • 1
    • 0001078943 scopus 로고
    • Salas, M.; Alvarez, M.; Joule, J. A., Heterocycles, 1991, 32, 759; Christopherson, C., "Marine alkaloids" in "The Alkaloids", Ed. Brossi, A., Academic Press, 1989, 24, 25; Fenical, W., Ch. 2 in "Alkaloids: chemical and biological perspectives", Pelletier, S. W., Ed., Wiley Interscience, NY, 1986, Vol. 3; Faulkner, D. J., Nat. Prod. Rep., 1984-1994; "Bioorganic Marine Chemistry", Ed. Scheuer , P. J., Springer-Verlag, Berlin, 1989; 'Ascidians: producers of amino acid derived metabolites', Davidson, B. S., Chem. Rev., 1993, 93, 1771; 'Marine pyridoacridine alkaloids: structure, synthesis, and biological chemistry', Molinski, T. F., Chem. Rev., 1993, 93, 1825.
    • (1991) Heterocycles , vol.32 , pp. 759
    • Salas, M.1    Alvarez, M.2    Joule, J.A.3
  • 2
    • 0008918521 scopus 로고
    • Marine alkaloids
    • Ed. Brossi, A., Academic Press
    • Salas, M.; Alvarez, M.; Joule, J. A., Heterocycles, 1991, 32, 759; Christopherson, C., "Marine alkaloids" in "The Alkaloids", Ed. Brossi, A., Academic Press, 1989, 24, 25; Fenical, W., Ch. 2 in "Alkaloids: chemical and biological perspectives", Pelletier, S. W., Ed., Wiley Interscience, NY, 1986, Vol. 3; Faulkner, D. J., Nat. Prod. Rep., 1984-1994; "Bioorganic Marine Chemistry", Ed. Scheuer , P. J., Springer-Verlag, Berlin, 1989; 'Ascidians: producers of amino acid derived metabolites', Davidson, B. S., Chem. Rev., 1993, 93, 1771; 'Marine pyridoacridine alkaloids: structure, synthesis, and biological chemistry', Molinski, T. F., Chem. Rev., 1993, 93, 1825.
    • (1989) The Alkaloids , vol.24 , pp. 25
    • Christopherson, C.1
  • 3
    • 0040158973 scopus 로고
    • Ch. 2, Pelletier, S. W., Ed., Wiley Interscience, NY
    • Salas, M.; Alvarez, M.; Joule, J. A., Heterocycles, 1991, 32, 759; Christopherson, C., "Marine alkaloids" in "The Alkaloids", Ed. Brossi, A., Academic Press, 1989, 24, 25; Fenical, W., Ch. 2 in "Alkaloids: chemical and biological perspectives", Pelletier, S. W., Ed., Wiley Interscience, NY, 1986, Vol. 3; Faulkner, D. J., Nat. Prod. Rep., 1984-1994; "Bioorganic Marine Chemistry", Ed. Scheuer , P. J., Springer-Verlag, Berlin, 1989; 'Ascidians: producers of amino acid derived metabolites', Davidson, B. S., Chem. Rev., 1993, 93, 1771; 'Marine pyridoacridine alkaloids: structure, synthesis, and biological chemistry', Molinski, T. F., Chem. Rev., 1993, 93, 1825.
    • (1986) Alkaloids: Chemical and Biological Perspectives , vol.3
    • Fenical, W.1
  • 4
    • 0006644076 scopus 로고
    • Salas, M.; Alvarez, M.; Joule, J. A., Heterocycles, 1991, 32, 759; Christopherson, C., "Marine alkaloids" in "The Alkaloids", Ed. Brossi, A., Academic Press, 1989, 24, 25; Fenical, W., Ch. 2 in "Alkaloids: chemical and biological perspectives", Pelletier, S. W., Ed., Wiley Interscience, NY, 1986, Vol. 3; Faulkner, D. J., Nat. Prod. Rep., 1984-1994; "Bioorganic Marine Chemistry", Ed. Scheuer , P. J., Springer-Verlag, Berlin, 1989; 'Ascidians: producers of amino acid derived metabolites', Davidson, B. S., Chem. Rev., 1993, 93, 1771; 'Marine pyridoacridine alkaloids: structure, synthesis, and biological chemistry', Molinski, T. F., Chem. Rev., 1993, 93, 1825.
    • (1984) Nat. Prod. Rep.
    • Faulkner, D.J.1
  • 5
    • 0038974750 scopus 로고
    • Springer-Verlag, Berlin
    • Salas, M.; Alvarez, M.; Joule, J. A., Heterocycles, 1991, 32, 759; Christopherson, C., "Marine alkaloids" in "The Alkaloids", Ed. Brossi, A., Academic Press, 1989, 24, 25; Fenical, W., Ch. 2 in "Alkaloids: chemical and biological perspectives", Pelletier, S. W., Ed., Wiley Interscience, NY, 1986, Vol. 3; Faulkner, D. J., Nat. Prod. Rep., 1984-1994; "Bioorganic Marine Chemistry", Ed. Scheuer , P. J., Springer-Verlag, Berlin, 1989; 'Ascidians: producers of amino acid derived metabolites', Davidson, B. S., Chem. Rev., 1993, 93, 1771; 'Marine pyridoacridine alkaloids: structure, synthesis, and biological chemistry', Molinski, T. F., Chem. Rev., 1993, 93, 1825.
    • (1989) Bioorganic Marine Chemistry
    • Scheuer, P.J.1
  • 6
    • 0000853969 scopus 로고
    • Ascidians: Producers of amino acid derived metabolites
    • Salas, M.; Alvarez, M.; Joule, J. A., Heterocycles, 1991, 32, 759; Christopherson, C., "Marine alkaloids" in "The Alkaloids", Ed. Brossi, A., Academic Press, 1989, 24, 25; Fenical, W., Ch. 2 in "Alkaloids: chemical and biological perspectives", Pelletier, S. W., Ed., Wiley Interscience, NY, 1986, Vol. 3; Faulkner, D. J., Nat. Prod. Rep., 1984-1994; "Bioorganic Marine Chemistry", Ed. Scheuer , P. J., Springer-Verlag, Berlin, 1989; 'Ascidians: producers of amino acid derived metabolites', Davidson, B. S., Chem. Rev., 1993, 93, 1771; 'Marine pyridoacridine alkaloids: structure, synthesis, and biological chemistry', Molinski, T. F., Chem. Rev., 1993, 93, 1825.
    • (1993) Chem. Rev. , vol.93 , pp. 1771
    • Davidson, B.S.1
  • 7
    • 0000331562 scopus 로고
    • Marine pyridoacridine alkaloids: Structure, synthesis, and biological chemistry
    • Salas, M.; Alvarez, M.; Joule, J. A., Heterocycles, 1991, 32, 759; Christopherson, C., "Marine alkaloids" in "The Alkaloids", Ed. Brossi, A., Academic Press, 1989, 24, 25; Fenical, W., Ch. 2 in "Alkaloids: chemical and biological perspectives", Pelletier, S. W., Ed., Wiley Interscience, NY, 1986, Vol. 3; Faulkner, D. J., Nat. Prod. Rep., 1984-1994; "Bioorganic Marine Chemistry", Ed. Scheuer , P. J., Springer-Verlag, Berlin, 1989; 'Ascidians: producers of amino acid derived metabolites', Davidson, B. S., Chem. Rev., 1993, 93, 1771; 'Marine pyridoacridine alkaloids: structure, synthesis, and biological chemistry', Molinski, T. F., Chem. Rev., 1993, 93, 1825.
    • (1993) Chem. Rev. , vol.93 , pp. 1825
    • Molinski, T.F.1
  • 11
    • 0022911007 scopus 로고
    • Perry, N. B.; Blunt, J. W.; McCombs, J. D.; Munro, M. H. G., J. Org. Chem., 1986, 51, 5476; Perry, N. B.; Blunt, J. W.; Munro, M. H. G., Tetrahedron, 1988, 44, 1727; Perry, N. B.; Blunt, J. W.; Munro, M. H. G.; Higa, T.; Sakai, R., J. Org. Chem., 1988, 53, 4127.
    • (1986) J. Org. Chem. , vol.51 , pp. 5476
    • Perry, N.B.1    Blunt, J.W.2    McCombs, J.D.3    Munro, M.H.G.4
  • 12
    • 0023918688 scopus 로고
    • Perry, N. B.; Blunt, J. W.; McCombs, J. D.; Munro, M. H. G., J. Org. Chem., 1986, 51, 5476; Perry, N. B.; Blunt, J. W.; Munro, M. H. G., Tetrahedron, 1988, 44, 1727; Perry, N. B.; Blunt, J. W.; Munro, M. H. G.; Higa, T.; Sakai, R., J. Org. Chem., 1988, 53, 4127.
    • (1988) Tetrahedron , vol.44 , pp. 1727
    • Perry, N.B.1    Blunt, J.W.2    Munro, M.H.G.3
  • 13
    • 0023682152 scopus 로고
    • Perry, N. B.; Blunt, J. W.; McCombs, J. D.; Munro, M. H. G., J. Org. Chem., 1986, 51, 5476; Perry, N. B.; Blunt, J. W.; Munro, M. H. G., Tetrahedron, 1988, 44, 1727; Perry, N. B.; Blunt, J. W.; Munro, M. H. G.; Higa, T.; Sakai, R., J. Org. Chem., 1988, 53, 4127.
    • (1988) J. Org. Chem. , vol.53 , pp. 4127
    • Perry, N.B.1    Blunt, J.W.2    Munro, M.H.G.3    Higa, T.4    Sakai, R.5
  • 20
    • 0027209179 scopus 로고
    • Venemalm, L.; Estévez, C.; Alvarez, M.; Joule, J. A., Tetrahedron Lett., 1993, 34, 5495; idem, Tetrahedron, 1994, 50, 7879; Balczewski, P.; Joule, J. A.; Estévez, C.; Alvarez, M., J. Org. Chem., 1994, 59, 4571; Roberts, D.; Venemalm, L.; Alvarez, M.; Joule, J. A., Tetrahedron Lett., 1994, 35, 7857.
    • (1993) Tetrahedron Lett. , vol.34 , pp. 5495
    • Venemalm, L.1    Estévez, C.2    Alvarez, M.3    Joule, J.A.4
  • 21
    • 0028228715 scopus 로고
    • Venemalm, L.; Estévez, C.; Alvarez, M.; Joule, J. A., Tetrahedron Lett., 1993, 34, 5495; idem, Tetrahedron, 1994, 50, 7879; Balczewski, P.; Joule, J. A.; Estévez, C.; Alvarez, M., J. Org. Chem., 1994, 59, 4571; Roberts, D.; Venemalm, L.; Alvarez, M.; Joule, J. A., Tetrahedron Lett., 1994, 35, 7857.
    • (1994) Tetrahedron , vol.50 , pp. 7879
    • Venemalm, L.1    Estévez, C.2    Alvarez, M.3    Joule, J.A.4
  • 22
    • 0027981577 scopus 로고
    • Venemalm, L.; Estévez, C.; Alvarez, M.; Joule, J. A., Tetrahedron Lett., 1993, 34, 5495; idem, Tetrahedron, 1994, 50, 7879; Balczewski, P.; Joule, J. A.; Estévez, C.; Alvarez, M., J. Org. Chem., 1994, 59, 4571; Roberts, D.; Venemalm, L.; Alvarez, M.; Joule, J. A., Tetrahedron Lett., 1994, 35, 7857.
    • (1994) J. Org. Chem. , vol.59 , pp. 4571
    • Balczewski, P.1    Joule, J.A.2    Estévez, C.3    Alvarez, M.4
  • 23
    • 0027944424 scopus 로고
    • Venemalm, L.; Estévez, C.; Alvarez, M.; Joule, J. A., Tetrahedron Lett., 1993, 34, 5495; idem, Tetrahedron, 1994, 50, 7879; Balczewski, P.; Joule, J. A.; Estévez, C.; Alvarez, M., J. Org. Chem., 1994, 59, 4571; Roberts, D.; Venemalm, L.; Alvarez, M.; Joule, J. A., Tetrahedron Lett., 1994, 35, 7857.
    • (1994) Tetrahedron Lett. , vol.35 , pp. 7857
    • Roberts, D.1    Venemalm, L.2    Alvarez, M.3    Joule, J.A.4
  • 25
    • 0000666009 scopus 로고
    • Hester, J. B., J. Org. Chem., 1964, 29, 1158; Hamabuchi, S.; Hamada, H.; Hironaka, A.; Somei, M., Heterocycles, 1991, 32, 443; Julia, M.; Huang, Y.; Igolen, J., C. R. Hebd. Seances Acad. Sci., 1967, 265, 110; Lee, F. G. H.; Daly, J. W.; Manian, A. A., J. Med. Chem., 1969, 12, 321.
    • (1964) J. Org. Chem. , vol.29 , pp. 1158
    • Hester, J.B.1
  • 26
    • 0040753099 scopus 로고
    • Hester, J. B., J. Org. Chem., 1964, 29, 1158; Hamabuchi, S.; Hamada, H.; Hironaka, A.; Somei, M., Heterocycles, 1991, 32, 443; Julia, M.; Huang, Y.; Igolen, J., C. R. Hebd. Seances Acad. Sci., 1967, 265, 110; Lee, F. G. H.; Daly, J. W.; Manian, A. A., J. Med. Chem., 1969, 12, 321.
    • (1991) Heterocycles , vol.32 , pp. 443
    • Hamabuchi, S.1    Hamada, H.2    Hironaka, A.3    Somei, M.4
  • 27
    • 64349120872 scopus 로고
    • Hester, J. B., J. Org. Chem., 1964, 29, 1158; Hamabuchi, S.; Hamada, H.; Hironaka, A.; Somei, M., Heterocycles, 1991, 32, 443; Julia, M.; Huang, Y.; Igolen, J., C. R. Hebd. Seances Acad. Sci., 1967, 265, 110; Lee, F. G. H.; Daly, J. W.; Manian, A. A., J. Med. Chem., 1969, 12, 321.
    • (1967) C. R. Hebd. Seances Acad. Sci. , vol.265 , pp. 110
    • Julia, M.1    Huang, Y.2    Igolen, J.3
  • 28
    • 0014487956 scopus 로고
    • Hester, J. B., J. Org. Chem., 1964, 29, 1158; Hamabuchi, S.; Hamada, H.; Hironaka, A.; Somei, M., Heterocycles, 1991, 32, 443; Julia, M.; Huang, Y.; Igolen, J., C. R. Hebd. Seances Acad. Sci., 1967, 265, 110; Lee, F. G. H.; Daly, J. W.; Manian, A. A., J. Med. Chem., 1969, 12, 321.
    • (1969) J. Med. Chem. , vol.12 , pp. 321
    • Lee, F.G.H.1    Daly, J.W.2    Manian, A.A.3
  • 40
    • 85029987955 scopus 로고    scopus 로고
    • note
    • 5 requires 296.0200.
  • 41
    • 85029998375 scopus 로고    scopus 로고
    • note
    • 4 requires 316.1190.
  • 42
    • 85029979259 scopus 로고    scopus 로고
    • note
    • 4 requires 308.0564.
  • 43
    • 85029987598 scopus 로고    scopus 로고
    • note
    • 2 requires 266.0822.
  • 44
    • 85029989347 scopus 로고    scopus 로고
    • note
    • 14b
  • 46
    • 85029992993 scopus 로고    scopus 로고
    • note
    • One resonance contributor only shown.
  • 47
    • 85029985623 scopus 로고    scopus 로고
    • note
    • An alternative is O-demethylation via chloride attack at the methyl group.
  • 48
    • 85029996769 scopus 로고    scopus 로고
    • note
    • The timing of acetal hydrolysis and pyrrole ring closure might be other than that shown.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.