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Volumn 2, Issue 13, 2004, Pages 1825-1826

A short synthesis of (±)-cytisine

Author keywords

[No Author keywords available]

Indexed keywords

ALKYLATION; CONFORMATIONS; ISOMERS; OLIGOMERS; PARAMETER ESTIMATION; SUBSTRATES; SYNTHESIS (CHEMICAL);

EID: 3142719015     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/b405275g     Document Type: Article
Times cited : (37)

References (28)
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    • N. J. Leonard, in The Alkaloids, ed. R. H. F. Manske and H. L. Holmes, Academic Press, New York, 1953, vol. 3, Chapter 19, p. 119; K. A. Aslanov, Y K. Kushmuradov and A. S. Sadykov, The Alkaloids, ed. A. Brossi, Academic Press, New York, 1997, vol. 31, Chapter 5, p. 117; H. C. S. Wood and R. Wrigglesworth, Rodd's Chemistry of Carbon Compounds, 2nd Edn., ed. S. Coffey, Elsevier, Amsterdam, 1978; Vol. IV, Part H, Chapter 38, p. 285.
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    • 77957086255 scopus 로고    scopus 로고
    • ed. A. Brossi, Academic Press, New York, Chapter 5
    • N. J. Leonard, in The Alkaloids, ed. R. H. F. Manske and H. L. Holmes, Academic Press, New York, 1953, vol. 3, Chapter 19, p. 119; K. A. Aslanov, Y K. Kushmuradov and A. S. Sadykov, The Alkaloids, ed. A. Brossi, Academic Press, New York, 1997, vol. 31, Chapter 5, p. 117; H. C. S. Wood and R. Wrigglesworth, Rodd's Chemistry of Carbon Compounds, 2nd Edn., ed. S. Coffey, Elsevier, Amsterdam, 1978; Vol. IV, Part H, Chapter 38, p. 285.
    • (1997) The Alkaloids , vol.31 , pp. 117
    • Aslanov, K.A.1    Kushmuradov, Y.K.2    Sadykov, A.S.3
  • 5
    • 77957086255 scopus 로고    scopus 로고
    • ed. S. Coffey, Elsevier, Amsterdam, Part H, Chapter 38
    • N. J. Leonard, in The Alkaloids, ed. R. H. F. Manske and H. L. Holmes, Academic Press, New York, 1953, vol. 3, Chapter 19, p. 119; K. A. Aslanov, Y K. Kushmuradov and A. S. Sadykov, The Alkaloids, ed. A. Brossi, Academic Press, New York, 1997, vol. 31, Chapter 5, p. 117; H. C. S. Wood and R. Wrigglesworth, Rodd's Chemistry of Carbon Compounds, 2nd Edn., ed. S. Coffey, Elsevier, Amsterdam, 1978; Vol. IV, Part H, Chapter 38, p. 285.
    • (1978) Rodd's Chemistry of Carbon Compounds, 2nd Edn. , vol.4 , pp. 285
    • Wood, H.C.S.1    Wrigglesworth, R.2
  • 15
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    • (b) J. W. Coe, Org. Lett., 2000, 2, 4205. A formal total synthesis based on ref. 6a has also been reported: P. Nshimyumukiza, D. Cahard, J. Rouden, M.-C. Lasne and J.-C. Plaquevent, Tetrahedron Lett., 2001, 42, 7787.
    • (2000) Org. Lett. , vol.2 , pp. 4205
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    • U.S. Patent 6,605,610
    • J. W. Coe and P. R. P. Brooks, U.S. Patent 6,605,610, 2003.
    • (2003)
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    • H. Liu, S. B. Ko, H. Josien and D. P. Curran, Tetrahedron Lett., 1995, 36, 8917. A variety of different conditions are presented in this paper, and a number of these were examined in our study. Alkyl halides tend to show lower JV-selectivities under conditions suited to more reactive allyl and propargyl halides.
    • (1995) Tetrahedron Lett. , vol.36 , pp. 8917
    • Liu, H.1    Ko, S.B.2    Josien, H.3    Curran, D.P.4
  • 23
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    • K. H. Shaughnessy, B. C. Hamann and J. F. Hartwig, J. Org. Chem., 1998, 63, 6546. See also T. Kama, X. Liu, D. A. Culkin and J. F. Hartwig, J. Am. Chem. Soc., 2003, 125, 11176; D. A. Culkin and J. F. Hartwig, Ace. Chem. Res., 2003, 36, 234.
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    • Shaughnessy, K.H.1    Hamann, B.C.2    Hartwig, J.F.3
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    • 0042693261 scopus 로고    scopus 로고
    • K. H. Shaughnessy, B. C. Hamann and J. F. Hartwig, J. Org. Chem., 1998, 63, 6546. See also T. Kama, X. Liu, D. A. Culkin and J. F. Hartwig, J. Am. Chem. Soc., 2003, 125, 11176; D. A. Culkin and J. F. Hartwig, Ace. Chem. Res., 2003, 36, 234.
    • (2003) J. Am. Chem. Soc. , vol.125 , pp. 11176
    • Kama, T.1    Liu, X.2    Culkin, D.A.3    Hartwig, J.F.4
  • 25
    • 0037393778 scopus 로고    scopus 로고
    • K. H. Shaughnessy, B. C. Hamann and J. F. Hartwig, J. Org. Chem., 1998, 63, 6546. See also T. Kama, X. Liu, D. A. Culkin and J. F. Hartwig, J. Am. Chem. Soc., 2003, 125, 11176; D. A. Culkin and J. F. Hartwig, Ace. Chem. Res., 2003, 36, 234.
    • (2003) Ace. Chem. Res. , vol.36 , pp. 234
    • Culkin, D.A.1    Hartwig, J.F.2
  • 26
    • 0037138675 scopus 로고    scopus 로고
    • (a) Buchwald has described the arylation of a vinylogous amide: T. Hamada, A. Chieffi, J. Ahman and S. L. Buchwald, J. Am. Chem. Soc., 2002, 124, 1261; (b) We also evaluated an alternative zinc-based variant that was recently reported, but without success See, J. Cossy, A. de Filippis and D. G. Pardo, Org. Lett., 2003, 5, 3037; δ -Lactams have been produced by intramolecular a-arylation of amide enolates, see T. Honda, H. Namiki and F.Satoh, Org. Leff., 2001,3, 631.
    • (2002) J. Am. Chem. Soc. , vol.124 , pp. 1261
    • Hamada, T.1    Chieffi, A.2    Ahman, J.3    Buchwald, S.L.4
  • 27
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    • (a) Buchwald has described the arylation of a vinylogous amide: T. Hamada, A. Chieffi, J. Ahman and S. L. Buchwald, J. Am. Chem. Soc., 2002, 124, 1261; (b) We also evaluated an alternative zinc-based variant that was recently reported, but without success See, J. Cossy, A. de Filippis and D. G. Pardo, Org. Lett., 2003, 5, 3037; δ -Lactams have been produced by intramolecular a-arylation of amide enolates, see T. Honda, H. Namiki and F.Satoh, Org. Leff., 2001,3, 631.
    • (2003) Org. Lett. , vol.5 , pp. 3037
    • Cossy, J.1    De Filippis, A.2    Pardo, D.G.3
  • 28
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    • (a) Buchwald has described the arylation of a vinylogous amide: T. Hamada, A. Chieffi, J. Ahman and S. L. Buchwald, J. Am. Chem. Soc., 2002, 124, 1261; (b) We also evaluated an alternative zinc-based variant that was recently reported, but without success See, J. Cossy, A. de Filippis and D. G. Pardo, Org. Lett., 2003, 5, 3037; δ -Lactams have been produced by intramolecular a-arylation of amide enolates, see T. Honda, H. Namiki and F.Satoh, Org. Leff., 2001,3, 631.
    • (2001) Org. Leff. , vol.3 , pp. 631
    • Honda, T.1    Namiki, H.2    Satoh, F.3


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