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Volumn 38, Issue 25, 1997, Pages 4437-4440

An asymmetric total synthesis of (-)-fumagillol

Author keywords

[No Author keywords available]

Indexed keywords

FUMAGILLIN;

EID: 0030986585     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00925-8     Document Type: Article
Times cited : (36)

References (21)
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    • Ingber, D. E.; Fujita, T.; Kishimoto, S.; Sudo, K.; Kanamaru, T.; Brem, H.; Folkman, J. Nature, 1990, 348, 555-557; Ingber, D. E. Semin. in Cancer Biol. 1992, 3, 57-63; Folkman, J.; Ingber, D. E. ibid. 1992, 3, 89-96.
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  • 7
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    • and references cited therein
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    • (1972) J. Am. Chem. Soc. , vol.94 , pp. 2549-2550
    • Corey, E.J.1    Snider, B.B.2
  • 8
    • 0001538420 scopus 로고
    • Burke, S. D.; Fobare, W. F.; Pacofsky, G. J. J. Org. Chem. 1983, 48, 5221-5228; Sato, T.; Tajima, K.; Fujisawa, T. Tetrahedron Lett. 1983, 24, 729-730; Kallmerten, J.; Gould, T. J. ibid. 1983, 24, 5177-5180.
    • (1983) J. Org. Chem. , vol.48 , pp. 5221-5228
    • Burke, S.D.1    Fobare, W.F.2    Pacofsky, G.J.3
  • 9
    • 0000268652 scopus 로고
    • Burke, S. D.; Fobare, W. F.; Pacofsky, G. J. J. Org. Chem. 1983, 48, 5221-5228; Sato, T.; Tajima, K.; Fujisawa, T. Tetrahedron Lett. 1983, 24, 729-730; Kallmerten, J.; Gould, T. J. ibid. 1983, 24, 5177-5180.
    • (1983) Tetrahedron Lett. , vol.24 , pp. 729-730
    • Sato, T.1    Tajima, K.2    Fujisawa, T.3
  • 10
    • 0001694854 scopus 로고
    • Burke, S. D.; Fobare, W. F.; Pacofsky, G. J. J. Org. Chem. 1983, 48, 5221-5228; Sato, T.; Tajima, K.; Fujisawa, T. Tetrahedron Lett. 1983, 24, 729-730; Kallmerten, J.; Gould, T. J. ibid. 1983, 24, 5177-5180.
    • (1983) Tetrahedron Lett. , vol.24 , pp. 5177-5180
    • Kallmerten, J.1    Gould, T.J.2
  • 11
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    • and references cited therein.
    • Kim, D.; Shin, K. J.; Kim, I. Y.; Park, S. W. Tetrahedron Lett. 1994, 35, 7957-7960 and references cited therein.; See also Stork, G. ; Zhao, K. J. Am. Chem. Soc. 1990, 112, 5875-5876.
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    • Kim, D.1    Shin, K.J.2    Kim, I.Y.3    Park, S.W.4
  • 12
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    • Kim, D.; Shin, K. J.; Kim, I. Y.; Park, S. W. Tetrahedron Lett. 1994, 35, 7957-7960 and references cited therein.; See also Stork, G. ; Zhao, K. J. Am. Chem. Soc. 1990, 112, 5875-5876.
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    • Stork, G.1    Zhao, K.2
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    • note
    • 1H NMR analysis and/or isolation of individual isomers.
  • 16
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    • note
    • A small amount of (Z)-enoate (about 5%) was present in the form of lactone 9′.
  • 18
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    • The stereoselectivity could be improved by the treatment of aldehyde 10 with (R,R)-diisopropyl tartrate-derived allylboronate in toluene at -78°C in the presence of 4A MS to give a 5.5 : 1 mixture of 5 and 5′ in 80% total yield: Roush, W. R.; Waltz, A. E.; Hoong, L. K. J. Am. Chem. Soc. 1985, 107, 8186-8190.
    • (1985) J. Am. Chem. Soc. , vol.107 , pp. 8186-8190
    • Roush, W.R.1    Waltz, A.E.2    Hoong, L.K.3
  • 21
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    • note
    • We thank Dr. S. Terao (Takeda Chemical Industries) for a generous sample of (-)-fumagillol.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.