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Volumn 82, Issue 2, 2010, Pages 1585-1600

A convenient entry to new C-7-modified colchicinoids through azide alkyne [3+2] cycloaddition: Application of ring-contractive rearrangements

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EID: 79952774430     PISSN: 03855414     EISSN: 18810942     Source Type: Journal    
DOI: 10.3987/COM-10-S(E)117     Document Type: Article
Times cited : (33)

References (40)
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    • (ed. by A. Brossi), Academic Press, Orlando, Chapter 1
    • H.-G. Capraro and A. Brossi in The Alkaloids, Vol. 23 (ed. by A. Brossi), Academic Press, Orlando, 1984, Chapter 1;
    • (1984) The Alkaloids , vol.23
    • Capraro, H.-G.1    Brossi, A.2
  • 8
    • 0004230722 scopus 로고
    • (ed. by A. Brossi and G. A. Cordell), Academic Press, San Diego, Chapter 3
    • O. Boyé and A. Brossi in The Alkaloids, Vol. 41 (ed. by A. Brossi and G. A. Cordell), Academic Press, San Diego, 1992, Chapter 3;
    • (1992) The Alkaloids , vol.41
    • Boyé, O.1    Brossi, A.2
  • 9
    • 0004237726 scopus 로고    scopus 로고
    • (ed. by G. A. Cordell), Academic Press, San Diego, Chapter 5
    • C. Le Hello in The Alkaloids, Vol. 53 (ed. by G. A. Cordell), Academic Press, San Diego, 2000, Chapter 5.
    • (2000) The Alkaloids , vol.53
    • Le Hello, C.1
  • 13
    • 4544293551 scopus 로고
    • see also: G. Quinkert (ed.), Synform, 1990, 8, 207.
    • (1990) Synform , vol.8 , pp. 207
    • Quinkert, G.1
  • 17
    • 14544286680 scopus 로고
    • ed. by R. H. F. Manske and H. L. Holmes, Academic Press, NY
    • J. W. Cook and J. D. Loudon in The Alkaloids Vol. 2, ed. by R. H. F. Manske and H. L. Holmes, Academic Press, NY, 1952, pp 261-329;
    • (1952) The Alkaloids , vol.2 , pp. 261-329
    • Cook, J.W.1    Loudon, J.D.2
  • 18
    • 79952753071 scopus 로고    scopus 로고
    • French, Patent 2848212
    • see also: Aventis Pharma, French Patent 2848212, 2002.
    • (2002) Aventis Pharma
  • 33
    • 11144325118 scopus 로고    scopus 로고
    • For the use of microwaves in organic synthesis, see: O. Kappe, Angew. Chem. Int. Ed., 2004, 43, 6250.
    • (2004) Angew. Chem. Int. Ed. , vol.43 , pp. 6250
    • Kappe, O.1
  • 38
    • 42449137851 scopus 로고    scopus 로고
    • In contrast to a misleading statement in the literature (Besong, D. Billen, I. Dager, P. Kocienski, E. Sliwinski, L. R. Tai, and F. T. Boyle, Tetrahedron, 2008, 64, 4700) the preparation of 9 through oxidative degradation under the Windaus conditions only works with colchiceine (2) as a substrate but not with colchicine (1) itself.
    • (2008) Tetrahedron , vol.64 , pp. 4700
    • Billen, D.1    Dager, I.2    Kocienski, P.3    Sliwinski, E.4    Tai, L.R.5    Boyle, F.T.6
  • 39
    • 0010741262 scopus 로고
    • 2. Ed., Verlag Chemie
    • The mechanism originally proposed by Fernholz (ref. 8) is not compatible with our modern understanding of organic reactions, but even in the famous textbook of L. Fieser and M. Fieser (Organische Chemie, 2. Ed., Verlag Chemie, 1968) the colchicine-allocolchicine rearrangement is (erroneously) classified as a benzilic acid rearrangement.
    • (1968) Organische Chemie
    • Fieser, L.1    Fieser, M.2
  • 40
    • 79952765363 scopus 로고    scopus 로고
    • note
    • Long before the theory of electrocyclic reactions was introduced by Woodward and Hoffmann (giving the cycloheptatriene-norcaradiene interconversion as an example) the fragmentation of a norcaradiene intermediate related to 22 was suggested by W. Leimgruber, Dissertation ETH Zürich 1959, footnote on p. 33. We are very grateful to Prof. A. Eschenmoser for bringing this to our attention. Also, in their seminal paper on tropolone (ref. 20), Doering and Knox already considered norcaradienes (drawn as resonance structures) participating in such rearrangements


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