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Volumn 128, Issue 21, 2006, Pages 6810-6812

α,β-unsaturated β-silyl lmide substrates for catalytic, enantioselective conjugate additions: A total synthesis of (+)-lactacystin and the discovery of a new proteasome inhibitor

Author keywords

[No Author keywords available]

Indexed keywords

BETA SILYL IMIDE; IMIDE; LACTACYSTIN; LACTAM; PROTEASOME INHIBITOR; SILANE DERIVATIVE; SPIRO BETA LACTONE; UNCLASSIFIED DRUG;

EID: 33744805367     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja061970a     Document Type: Article
Times cited : (141)

References (50)
  • 1
    • 33744795339 scopus 로고    scopus 로고
    • Thieine: Stuttgart
    • For a review, see: Fleming. I. Science of Synthexis: Thieine: Stuttgart, 2002; Vol. 4. pp 927-946.
    • (2002) Science of Synthexis , vol.4 , pp. 927-946
    • Fleming, I.1
  • 4
    • 0026471806 scopus 로고
    • For isolated examples of β-silyl carbonyl derivatives formed by asymmetric catalytic methods, see: (a) Martin, S. F.; Oalmann, C. J.; Liras, S. Tetrahedron Lett. 1992, 33, 6727-6730.
    • (1992) Tetrahedron Lett. , vol.33 , pp. 6727-6730
    • Martin, S.F.1    Oalmann, C.J.2    Liras, S.3
  • 9
    • 0000679263 scopus 로고    scopus 로고
    • Jacobsen, E. N., Pfalz, A., Yamamoto, H., Eds.; Springer: Berlin, Chapters 31.1 and 31.2
    • For reviews on enantioselective conjugate addition reactions, see: (a) Tomioka, K.; Nagaoka, Y.; Yamaguchi, M. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfalz, A., Yamamoto, H., Eds.; Springer: Berlin, 1999; Vol. 3, Chapters 31.1 and 31.2.
    • (1999) Comprehensive Asymmetric Catalysis , vol.3
    • Tomioka, K.1    Nagaoka, Y.2    Yamaguchi, M.3
  • 11
    • 0027958642 scopus 로고
    • and references therein
    • For catalytic, enantioselective conjugate additions using silicon-containing substrates, see: (a) Masumoto, Y.; Hayashi, T.; Ito, Y. Tetrahedron 1994, 50, 335-346 and references therein.
    • (1994) Tetrahedron , vol.50 , pp. 335-346
    • Masumoto, Y.1    Hayashi, T.2    Ito, Y.3
  • 29
    • 33744827889 scopus 로고    scopus 로고
    • note
    • For details of imide synthesis, see Supporting Information.
  • 34
    • 33744796719 scopus 로고    scopus 로고
    • To our knowledge, there has been only one prior synthesis of the 1-oxo-2-oxa-5-azaspiro[3.4]octane ring system: Papillon, J. P. N.; Taylor, R. J. K. Org. Lett. 2000, 2, 1978-1990.
    • (2000) Org. Lett. , vol.2 , pp. 1978-1990
    • Papillon, J.P.N.1    Taylor, R.J.K.2
  • 44
    • 33744789067 scopus 로고    scopus 로고
    • note
    • For details of the synthesis of 12, see Supporting Information.
  • 45
    • 27644518292 scopus 로고    scopus 로고
    • Deshaies, R. J., Ed.; Elsevier: Amsterdam
    • (a) Kisselev, A. F.; Goldberg, A. L. In Methods of Emymology; Deshaies, R. J., Ed.; Elsevier: Amsterdam, 2005; Vol. 398, pp 364-378.
    • (2005) Methods of Emymology , vol.398 , pp. 364-378
    • Kisselev, A.F.1    Goldberg, A.L.2
  • 47
    • 33744786695 scopus 로고    scopus 로고
    • note
    • β-Lactone 11 does not undergo conversion to 3 upon long-term storage as a stock solution in DMSO; we are currently investigating its behavior under assay conditions.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.