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Volumn , Issue 8, 1989, Pages 518-520

Non-oxidative methodology for the synthesis of vinblastine and vincristine models

Author keywords

[No Author keywords available]

Indexed keywords

VINCA ALKALOID;

EID: 0024573876     PISSN: 00224936     EISSN: None     Source Type: Journal    
DOI: 10.1039/C39890000518     Document Type: Article
Times cited : (35)

References (43)
  • 1
    • 0003564536 scopus 로고
    • J. M. Cassady and J. D. Douros, Academic Press, New York
    • For an authoritative review see: K. Gerzon, in ‘Anti-Cancer Agents Based on Natural Product Models,’ eds. J. M. Cassady and J. D. Douros, Academic Press, New York, 1980.
    • (1980) Anti-Cancer Agents Based on Natural Product Models
    • Gerzon, K.1
  • 7
    • 0023640651 scopus 로고
    • For the synthesis of 20′-desethyl-20′-deoxyvinblastine using a modification of the chloroindolenine route that produces the correct C(16’S) configuration
    • For the synthesis of 20′-desethyl-20′-deoxyvinblastine using a modification of the chloroindolenine route that produces the correct C(16’S) configuration: M. E. Kuehne, T. C. Zebovitz, W. G. Bornmann, and I. Marko, J. Org. Chem., 1987, 52, 4340.
    • (1987) J. Org. Chem , vol.52 , pp. 4340
    • Kuehne, M.E.1    Zebovitz, T.C.2    Bornmann, W.G.3    Marko, I.4
  • 8
    • 0003286012 scopus 로고
    • This approach is based upon the Levy system. Recent work using the chloroindolenine method has been applied to analogues: G. Schill. C. U. Priester
    • This approach is based upon the Levy system. M. Döe de Maindreville and J. Levy, Bull. Soc. Chim. Fr., 1981, 179: Recent work using the chloroindolenine method has been applied to analogues: G. Schill. C. U. Priester.
    • (1981) Bull. Soc. Chim. Fr , pp. 179
    • Döe de Maindreville, M.1    Levy, J.2
  • 12
    • 0017347374 scopus 로고
    • For review articles on the coupling reaction
    • For review articles on the coupling reaction: J. P. Kutney, Lloydia, 1977, 40, 107.
    • (1977) Lloydia , vol.40 , pp. 107
    • Kutney, J.P.1
  • 26
    • 0000755058 scopus 로고
    • This reference describes the ethyl ester of (5)
    • E. Wenkert, S. Garratt, and K. G. Dave, Can. J. Chem., 1964, 42, 489. This reference describes the ethyl ester of (5).
    • (1964) Can. J. Chem , vol.42 , pp. 489
    • Wenkert, E.1    Garratt, S.2    Dave, K.G.3
  • 27
    • 0009709215 scopus 로고
    • The 1H n.m.r. spectrum of (8) (as an example) at 20 °C shows four OMe signals attributable to the CO2Me group. At 35-40°C the four signals become two and at 60-70 °C a broad singlet appears. The process is reversible upon cooling. The free energy of activation associated with carbamate resonance has been determined by n.m.r. spectroscopic methods to be approximately 16 kcal mol-1 (1 cal = 4.184J)
    • The 1H n.m.r. spectrum of (8) (as an example) at 20 °C shows four OMe signals attributable to the CO2Me group. At 35-40°C the four signals become two and at 60-70 °C a broad singlet appears. The process is reversible upon cooling. The free energy of activation associated with carbamate resonance has been determined by n.m.r. spectroscopic methods to be approximately 16 kcal mol-1 (1 cal = 4.184J). B. J. Price, R. V. Smallman, and I. O. Sutherland, J. Chem. Soc., Chem. Comm., 1966, 319.
    • (1966) J. Chem. Soc., Chem. Comm , pp. 319
    • Price, B.J.1    Smallman, R.V.2    Sutherland, I.O.3
  • 28
    • 32344435180 scopus 로고
    • The Study of Intramolecular Rate Processes by Dynamic Nuclear Magnetic Resonance
    • G. Binsch in eds. E. L. Eliel and N. L. Allinger Wiley Interscience, New York
    • ‘The Study of Intramolecular Rate Processes by Dynamic Nuclear Magnetic Resonance,’ G. Binsch in ‘Topics in Stereochemistry,’ eds. E. L. Eliel and N. L. Allinger, Vol. 3, Wiley Interscience, New York, 1968.
    • (1968) Topics in Stereochemistry , vol.3
  • 29
    • 37049120467 scopus 로고
    • Assignment of absolute configuration at C(16’) is made by comparison of the CD curves with vinblastine
    • Assignment of absolute configuration at C(16’) is made by comparison of the CD curves with vinblastine: P. Potier, N. Langlois, Y. Langlois, and F. Guéritte, J. Chem. Soc., Chem. Comm., 1975, 670.
    • (1975) J. Chem. Soc., Chem. Comm , pp. 670
    • Potier, P.1    Langlois, N.2    Langlois, Y.3    Guéritte, F.4
  • 33
    • 33845281351 scopus 로고
    • The stabilization of propargylic cations by Co2(CO)6 has been reviewed
    • The stabilization of propargylic cations by Co2(CO)6 has been reviewed: K. M. Nicholas, Acc. Chem. Res., 1987, 20, 207.
    • (1987) Acc. Chem. Res , vol.20 , pp. 207
    • Nicholas, K.M.1
  • 35
    • 84943030553 scopus 로고
    • The Study of Optically Labile Compounds
    • M. M. Harris, eds. W. Klyne and P. B. D. de la Mare, Butterworths, New York
    • K. M. Nicholas, M. Mulraney, and M. Bayer, ‘The Study of Optically Labile Compounds,’ M. M. Harris, in ‘Progress in Stereochemistry,’ eds. W. Klyne and P. B. D. de la Mare, Vol. 2, p. 157, Butterworths, New York, 1958.
    • (1958) Progress in Stereochemistry , vol.2
    • Nicholas, K.M.1    Mulraney, M.2    Bayer, M.3
  • 37
    • 51149206079 scopus 로고
    • The closest systems described in the literature are in the thebaine alkaloid area, for example, phenyldihydrothebaine
    • The closest systems described in the literature are in the thebaine alkaloid area, for example, phenyldihydrothebaine: R. Robinson, Nature Lond., 1947, 160, 815.
    • (1947) Nature Lond , vol.160 , pp. 815
    • Robinson, R.1
  • 41


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