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Volumn 44, Issue 17, 2003, Pages 3569-3572

Total synthesis of the novel angiogenesis inhibitors epoxyquinols A and B

Author keywords

[No Author keywords available]

Indexed keywords

1,4 BENZOQUINONE; ANGIOGENESIS INHIBITOR; CYCLOPENTADIENE DERIVATIVE; DIMER; EPOXYQUINOL A; EPOXYQUINOL B; POLYKETIDE; UNCLASSIFIED DRUG;

EID: 0037459852     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)00621-X     Document Type: Article
Times cited : (59)

References (19)
  • 5
    • 0031955249 scopus 로고    scopus 로고
    • Selected references: (a) Taylor, R. J. K.; Alkaraz, L.; Kapfer-Eyer, I.; Macdonald, G.; Wei, X.; Lewis, N. Synthesis 1998, 775; (b) Kamikubo, T.; Ogaswara, K. Chem. Commun. 1996, 1679; (c) Kamikubo, T.; Hiroya, K.; Ogaswara, K. Tetrahedron Lett. 1996, 37, 499; (d) Li, C.; Lobskovsky, E.; Porco, J. A. Am. Chem. Soc. 2000, 122, 10484; (e) Genski, T.; Taylor, R. J. K. Tetrahedron Lett. 2002, 43, 3573.
    • (1998) Synthesis , pp. 775
    • Taylor, R.J.K.1    Alkaraz, L.2    Kapfer-Eyer, I.3    Macdonald, G.4    Wei, X.5    Lewis, N.6
  • 6
    • 0029935883 scopus 로고    scopus 로고
    • Selected references: (a) Taylor, R. J. K.; Alkaraz, L.; Kapfer-Eyer, I.; Macdonald, G.; Wei, X.; Lewis, N. Synthesis 1998, 775; (b) Kamikubo, T.; Ogaswara, K. Chem. Commun. 1996, 1679; (c) Kamikubo, T.; Hiroya, K.; Ogaswara, K. Tetrahedron Lett. 1996, 37, 499; (d) Li, C.; Lobskovsky, E.; Porco, J. A. Am. Chem. Soc. 2000, 122, 10484; (e) Genski, T.; Taylor, R. J. K. Tetrahedron Lett. 2002, 43, 3573.
    • (1996) Chem. Commun. , pp. 1679
    • Kamikubo, T.1    Ogaswara, K.2
  • 7
    • 0030033034 scopus 로고    scopus 로고
    • Selected references: (a) Taylor, R. J. K.; Alkaraz, L.; Kapfer-Eyer, I.; Macdonald, G.; Wei, X.; Lewis, N. Synthesis 1998, 775; (b) Kamikubo, T.; Ogaswara, K. Chem. Commun. 1996, 1679; (c) Kamikubo, T.; Hiroya, K.; Ogaswara, K. Tetrahedron Lett. 1996, 37, 499; (d) Li, C.; Lobskovsky, E.; Porco, J. A. Am. Chem. Soc. 2000, 122, 10484; (e) Genski, T.; Taylor, R. J. K. Tetrahedron Lett. 2002, 43, 3573.
    • (1996) Tetrahedron Lett. , vol.37 , pp. 499
    • Kamikubo, T.1    Hiroya, K.2    Ogaswara, K.3
  • 8
    • 0034715469 scopus 로고    scopus 로고
    • Selected references: (a) Taylor, R. J. K.; Alkaraz, L.; Kapfer-Eyer, I.; Macdonald, G.; Wei, X.; Lewis, N. Synthesis 1998, 775; (b) Kamikubo, T.; Ogaswara, K. Chem. Commun. 1996, 1679; (c) Kamikubo, T.; Hiroya, K.; Ogaswara, K. Tetrahedron Lett. 1996, 37, 499; (d) Li, C.; Lobskovsky, E.; Porco, J. A. Am. Chem. Soc. 2000, 122, 10484; (e) Genski, T.; Taylor, R. J. K. Tetrahedron Lett. 2002, 43, 3573.
    • (2000) A. Am. Chem. Soc. , vol.122 , pp. 10484
    • Li, C.1    Lobskovsky, E.2    Porco, J.3
  • 9
    • 0037029830 scopus 로고    scopus 로고
    • Selected references: (a) Taylor, R. J. K.; Alkaraz, L.; Kapfer-Eyer, I.; Macdonald, G.; Wei, X.; Lewis, N. Synthesis 1998, 775; (b) Kamikubo, T.; Ogaswara, K. Chem. Commun. 1996, 1679; (c) Kamikubo, T.; Hiroya, K.; Ogaswara, K. Tetrahedron Lett. 1996, 37, 499; (d) Li, C.; Lobskovsky, E.; Porco, J. A. Am. Chem. Soc. 2000, 122, 10484; (e) Genski, T.; Taylor, R. J. K. Tetrahedron Lett. 2002, 43, 3573.
    • (2002) Tetrahedron Lett. , vol.43 , pp. 3573
    • Genski, T.1    Taylor, R.J.K.2
  • 15
    • 85031202293 scopus 로고    scopus 로고
    • note
    • 13C NMR, Mass).
  • 17
    • 85031200248 scopus 로고    scopus 로고
    • o) and 0.0521 for all 5232
    • 2=0.1129, GOF=1.042. Restrained GOF=1.042 for all data. Crystallographic data (without structure factors) have been deposited with the Cambridge Crystallographic Data Center and the depository number is CCDC 199400. ORTEP diagrams of 13 and 16 are shown above.
  • 18
    • 85031203712 scopus 로고    scopus 로고
    • We have elaborated the Z-isomer 17 to a new Z-epoxyquinol corresponding to 5 and its chemistry is being investigated.
    • We have elaborated the Z-isomer 17 to a new Z-epoxyquinol corresponding to 5 and its chemistry is being investigated.
  • 19
    • 85031209526 scopus 로고    scopus 로고
    • 4 have found that transformation of 4 to furnish 1 and 2 via 3a,b is quite sensitive to time, temperature and solvent regimes and efforts are underway to optimize the conditions for this process.
    • 4 have found that transformation of 4 to furnish 1 and 2 via 3a,b is quite sensitive to time, temperature and solvent regimes and efforts are underway to optimize the conditions for this process.


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