메뉴 건너뛰기




Volumn 38, Issue 39, 1997, Pages 6909-6912

A new method for the formation of the imidazo[4',5';3,4]pyrido[2,3-b]indole ring: Formal synthesis of the alkaloids from marine origin grossularines -1 and 2

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOID; CARBOLINE DERIVATIVE; GROSSULARINE 1; GROSSULARINE 2; UNCLASSIFIED DRUG;

EID: 0030751339     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)01592-X     Document Type: Article
Times cited : (17)

References (22)
  • 2
    • 0025076413 scopus 로고
    • For recent reports of biologically active 2-aminoimidazole alkaloids, see: Kobayashi, J.; Tsuda, M.; Murayama, T.; Nakamura, H.; Ohizumi, Y.; Ishibashi, M.; Iwamura, M.; Otha, T.; Nozoe, S. Tetrahedron 1990, 46, 5579. Commerço, A.; Gueremy, C. Tetrahedron Lett. 1991, 32, 1416. He, H.; Faulkner, D. J.; Lee, A.; Clardy, J. J. Org. Chem. 1992, 57, 2176. Faulkner, D. J.; Nat. Prod. Rep. 1992, 9, 323. Alvi, K. A.; Peters, B. M.; Hunter, L. M.; Crews, P. Tetrahedron 1993, 49, 329. Little, T. L.; Webber, S.E. J. Org. Chem. 1994, 59, 7299. Chan, G.W.; Mong, S.; Hemling, M. E.; Freyer, A. J.; Offen, P.H.; DeBrosse, C. W.; Sarau, H. M.; Westley, J. W. J. Nat. Prod. 1993, 56, 116.
    • (1990) Tetrahedron , vol.46 , pp. 5579
    • Kobayashi, J.1    Tsuda, M.2    Murayama, T.3    Nakamura, H.4    Ohizumi, Y.5    Ishibashi, M.6    Iwamura, M.7    Otha, T.8    Nozoe, S.9
  • 3
    • 8044255616 scopus 로고
    • For recent reports of biologically active 2-aminoimidazole alkaloids, see: Kobayashi, J.; Tsuda, M.; Murayama, T.; Nakamura, H.; Ohizumi, Y.; Ishibashi, M.; Iwamura, M.; Otha, T.; Nozoe, S. Tetrahedron 1990, 46, 5579. Commerço, A.; Gueremy, C. Tetrahedron Lett. 1991, 32, 1416. He, H.; Faulkner, D. J.; Lee, A.; Clardy, J. J. Org. Chem. 1992, 57, 2176. Faulkner, D. J.; Nat. Prod. Rep. 1992, 9, 323. Alvi, K. A.; Peters, B. M.; Hunter, L. M.; Crews, P. Tetrahedron 1993, 49, 329. Little, T. L.; Webber, S.E. J. Org. Chem. 1994, 59, 7299. Chan, G.W.; Mong, S.; Hemling, M. E.; Freyer, A. J.; Offen, P.H.; DeBrosse, C. W.; Sarau, H. M.; Westley, J. W. J. Nat. Prod. 1993, 56, 116.
    • (1991) Tetrahedron Lett. , vol.32 , pp. 1416
    • Commerço, A.1    Gueremy, C.2
  • 4
    • 0001649051 scopus 로고
    • For recent reports of biologically active 2-aminoimidazole alkaloids, see: Kobayashi, J.; Tsuda, M.; Murayama, T.; Nakamura, H.; Ohizumi, Y.; Ishibashi, M.; Iwamura, M.; Otha, T.; Nozoe, S. Tetrahedron 1990, 46, 5579. Commerço, A.; Gueremy, C. Tetrahedron Lett. 1991, 32, 1416. He, H.; Faulkner, D. J.; Lee, A.; Clardy, J. J. Org. Chem. 1992, 57, 2176. Faulkner, D. J.; Nat. Prod. Rep. 1992, 9, 323. Alvi, K. A.; Peters, B. M.; Hunter, L. M.; Crews, P. Tetrahedron 1993, 49, 329. Little, T. L.; Webber, S.E. J. Org. Chem. 1994, 59, 7299. Chan, G.W.; Mong, S.; Hemling, M. E.; Freyer, A. J.; Offen, P.H.; DeBrosse, C. W.; Sarau, H. M.; Westley, J. W. J. Nat. Prod. 1993, 56, 116.
    • (1992) J. Org. Chem. , vol.57 , pp. 2176
    • He, H.1    Faulkner, D.J.2    Lee, A.3    Clardy, J.4
  • 5
    • 0000372491 scopus 로고
    • For recent reports of biologically active 2-aminoimidazole alkaloids, see: Kobayashi, J.; Tsuda, M.; Murayama, T.; Nakamura, H.; Ohizumi, Y.; Ishibashi, M.; Iwamura, M.; Otha, T.; Nozoe, S. Tetrahedron 1990, 46, 5579. Commerço, A.; Gueremy, C. Tetrahedron Lett. 1991, 32, 1416. He, H.; Faulkner, D. J.; Lee, A.; Clardy, J. J. Org. Chem. 1992, 57, 2176. Faulkner, D. J.; Nat. Prod. Rep. 1992, 9, 323. Alvi, K. A.; Peters, B. M.; Hunter, L. M.; Crews, P. Tetrahedron 1993, 49, 329. Little, T. L.; Webber, S.E. J. Org. Chem. 1994, 59, 7299. Chan, G.W.; Mong, S.; Hemling, M. E.; Freyer, A. J.; Offen, P.H.; DeBrosse, C. W.; Sarau, H. M.; Westley, J. W. J. Nat. Prod. 1993, 56, 116.
    • (1992) Nat. Prod. Rep. , vol.9 , pp. 323
    • Faulkner, D.J.1
  • 6
    • 0027529720 scopus 로고
    • For recent reports of biologically active 2-aminoimidazole alkaloids, see: Kobayashi, J.; Tsuda, M.; Murayama, T.; Nakamura, H.; Ohizumi, Y.; Ishibashi, M.; Iwamura, M.; Otha, T.; Nozoe, S. Tetrahedron 1990, 46, 5579. Commerço, A.; Gueremy, C. Tetrahedron Lett. 1991, 32, 1416. He, H.; Faulkner, D. J.; Lee, A.; Clardy, J. J. Org. Chem. 1992, 57, 2176. Faulkner, D. J.; Nat. Prod. Rep. 1992, 9, 323. Alvi, K. A.; Peters, B. M.; Hunter, L. M.; Crews, P. Tetrahedron 1993, 49, 329. Little, T. L.; Webber, S.E. J. Org. Chem. 1994, 59, 7299. Chan, G.W.; Mong, S.; Hemling, M. E.; Freyer, A. J.; Offen, P.H.; DeBrosse, C. W.; Sarau, H. M.; Westley, J. W. J. Nat. Prod. 1993, 56, 116.
    • (1993) Tetrahedron , vol.49 , pp. 329
    • Alvi, K.A.1    Peters, B.M.2    Hunter, L.M.3    Crews, P.4
  • 7
    • 0028600543 scopus 로고
    • For recent reports of biologically active 2-aminoimidazole alkaloids, see: Kobayashi, J.; Tsuda, M.; Murayama, T.; Nakamura, H.; Ohizumi, Y.; Ishibashi, M.; Iwamura, M.; Otha, T.; Nozoe, S. Tetrahedron 1990, 46, 5579. Commerço, A.; Gueremy, C. Tetrahedron Lett. 1991, 32, 1416. He, H.; Faulkner, D. J.; Lee, A.; Clardy, J. J. Org. Chem. 1992, 57, 2176. Faulkner, D. J.; Nat. Prod. Rep. 1992, 9, 323. Alvi, K. A.; Peters, B. M.; Hunter, L. M.; Crews, P. Tetrahedron 1993, 49, 329. Little, T. L.; Webber, S.E. J. Org. Chem. 1994, 59, 7299. Chan, G.W.; Mong, S.; Hemling, M. E.; Freyer, A. J.; Offen, P.H.; DeBrosse, C. W.; Sarau, H. M.; Westley, J. W. J. Nat. Prod. 1993, 56, 116.
    • (1994) J. Org. Chem. , vol.59 , pp. 7299
    • Little, T.L.1    Webber, S.E.2
  • 8
    • 0027348616 scopus 로고
    • For recent reports of biologically active 2-aminoimidazole alkaloids, see: Kobayashi, J.; Tsuda, M.; Murayama, T.; Nakamura, H.; Ohizumi, Y.; Ishibashi, M.; Iwamura, M.; Otha, T.; Nozoe, S. Tetrahedron 1990, 46, 5579. Commerço, A.; Gueremy, C. Tetrahedron Lett. 1991, 32, 1416. He, H.; Faulkner, D. J.; Lee, A.; Clardy, J. J. Org. Chem. 1992, 57, 2176. Faulkner, D. J.; Nat. Prod. Rep. 1992, 9, 323. Alvi, K. A.; Peters, B. M.; Hunter, L. M.; Crews, P. Tetrahedron 1993, 49, 329. Little, T. L.; Webber, S.E. J. Org. Chem. 1994, 59, 7299. Chan, G.W.; Mong, S.; Hemling, M. E.; Freyer, A. J.; Offen, P.H.; DeBrosse, C. W.; Sarau, H. M.; Westley, J. W. J. Nat. Prod. 1993, 56, 116.
    • (1993) J. Nat. Prod. , vol.56 , pp. 116
    • Chan, G.W.1    Mong, S.2    Hemling, M.E.3    Freyer, A.J.4    Offen, P.H.5    DeBrosse, C.W.6    Sarau, H.M.7    Westley, J.W.8
  • 16
    • 0026653738 scopus 로고
    • Molina, P.; Fresneda, P. M.; Almendros, P. Tetrahedron Lett. 1992, 3, 4491. Molina, P.; Almendros, P.; Fresneda, P. M. Tetrahedron 1994, 50, 2241. Molina, P.; Almendros, P.; Fresneda, P. M. Tetrahedron Lett. 1994, 35, 2235.
    • (1992) Tetrahedron Lett. , vol.3 , pp. 4491
    • Molina, P.1    Fresneda, P.M.2    Almendros, P.3
  • 17
    • 0028270313 scopus 로고
    • Molina, P.; Fresneda, P. M.; Almendros, P. Tetrahedron Lett. 1992, 3, 4491. Molina, P.; Almendros, P.; Fresneda, P. M. Tetrahedron 1994, 50, 2241. Molina, P.; Almendros, P.; Fresneda, P. M. Tetrahedron Lett. 1994, 35, 2235.
    • (1994) Tetrahedron , vol.50 , pp. 2241
    • Molina, P.1    Almendros, P.2    Fresneda, P.M.3
  • 18
    • 0028351776 scopus 로고
    • Molina, P.; Fresneda, P. M.; Almendros, P. Tetrahedron Lett. 1992, 3, 4491. Molina, P.; Almendros, P.; Fresneda, P. M. Tetrahedron 1994, 50, 2241. Molina, P.; Almendros, P.; Fresneda, P. M. Tetrahedron Lett. 1994, 35, 2235.
    • (1994) Tetrahedron Lett. , vol.35 , pp. 2235
    • Molina, P.1    Almendros, P.2    Fresneda, P.M.3
  • 20
    • 0342564500 scopus 로고    scopus 로고
    • note
    • tBu), 187.4 (CO). IR (nujol) ν : 3268 (m), 1733 (s), 1620 (s).
  • 21
    • 0343870203 scopus 로고    scopus 로고
    • note
    • 2O), 99.4 (q), 109.9 (C-7), 116.0 (q), 119.8 (C-9), 120.7 (C-10), 121.0 (q), 121.9 (q), 122.9 (C-8), 136.9 (q), 148.2 (q), 151.5 (q), 154.6 (q). IR (nujol) ν : 3344(m), 1684(m), 1597(s). MS: m/z(%) (FAB positive, NBA) 312 (M+H, 100); (EI posi live) 312 (M+1, 23), 311 (M, 100), 280 (49), 266 (22).
  • 22
    • 0343870201 scopus 로고
    • Katritzky, A. R.; Meth-Cohn, O.; Rees, C. W. Ed.; Moody, C. J., vol. Ed.; Pergamon : Cambridge
    • Molina, P.; Tarraga, A. Comprehensive Organic Functional Group Transformations ; Katritzky, A. R.; Meth-Cohn, O.; Rees, C. W. Ed.; Vol. 5; Moody, C. J., vol. Ed.; Pergamon : Cambridge, 1995; p 976.
    • (1995) Comprehensive Organic Functional Group Transformations , vol.5 , pp. 976
    • Molina, P.1    Tarraga, A.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.