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Crystallographic data (excluding structure factors) for the structure reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC-124114. Copies of the data can be obtained free of charge on application to CCDC, 12 Union Rd., Cambridge, CB2 1EZ, U.K. [Fax: (internat.) + 44-1223/336-033; E-mail: deposit@ccdc.cam.ac.uk].
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0003145667
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Recent examples of 5-endo-trig cyclizations: M. B. Berry, D. Craig, P. S. Jones, G. J. Rowlands, J. Chem. Soc., Chem. Commun. 1997, 2141-2142; D. Craig, P. S. Jones, G. J. Rowlands, Synlett 1997, 1423-1425; D. Craig, N. J. Ikin, N. Mathews, A. M. Smith, Tetrahedron Lett. 1995, 36, 7531-7534; D. Craig, A. M. Smith, Tetrahedron Lett. 1992, 33, 695-698; A. Padwa, B. H. Norman, J. Org. Chem. 1990, 55, 4801-4807; Tetrahedron Lett. 1988, 29, 3041-3044; S.-S. P. Chou, T.-M. Yuan, Synthesis 1991, 171-172; A. D. Jones, D. W. Knight J. Chem. Soc., Chem. Commun. 1996, 915-916; D. W. Knight, A. L. Redfern, J. Gilmore, Tetrahedron Lett. 1998, 39, 8909-8910.
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Recent examples of 5-endo-trig cyclizations: M. B. Berry, D. Craig, P. S. Jones, G. J. Rowlands, J. Chem. Soc., Chem. Commun. 1997, 2141-2142; D. Craig, P. S. Jones, G. J. Rowlands, Synlett 1997, 1423-1425; D. Craig, N. J. Ikin, N. Mathews, A. M. Smith, Tetrahedron Lett. 1995, 36, 7531-7534; D. Craig, A. M. Smith, Tetrahedron Lett. 1992, 33, 695-698; A. Padwa, B. H. Norman, J. Org. Chem. 1990, 55, 4801-4807; Tetrahedron Lett. 1988, 29, 3041-3044; S.-S. P. Chou, T.-M. Yuan, Synthesis 1991, 171-172; A. D. Jones, D. W. Knight J. Chem. Soc., Chem. Commun. 1996, 915-916; D. W. Knight, A. L. Redfern, J. Gilmore, Tetrahedron Lett. 1998, 39, 8909-8910.
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Recent examples of 5-endo-trig cyclizations: M. B. Berry, D. Craig, P. S. Jones, G. J. Rowlands, J. Chem. Soc., Chem. Commun. 1997, 2141-2142; D. Craig, P. S. Jones, G. J. Rowlands, Synlett 1997, 1423-1425; D. Craig, N. J. Ikin, N. Mathews, A. M. Smith, Tetrahedron Lett. 1995, 36, 7531-7534; D. Craig, A. M. Smith, Tetrahedron Lett. 1992, 33, 695-698; A. Padwa, B. H. Norman, J. Org. Chem. 1990, 55, 4801-4807; Tetrahedron Lett. 1988, 29, 3041-3044; S.-S. P. Chou, T.-M. Yuan, Synthesis 1991, 171-172; A. D. Jones, D. W. Knight J. Chem. Soc., Chem. Commun. 1996, 915-916; D. W. Knight, A. L. Redfern, J. Gilmore, Tetrahedron Lett. 1998, 39, 8909-8910.
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Recent examples of 5-endo-trig cyclizations: M. B. Berry, D. Craig, P. S. Jones, G. J. Rowlands, J. Chem. Soc., Chem. Commun. 1997, 2141-2142; D. Craig, P. S. Jones, G. J. Rowlands, Synlett 1997, 1423-1425; D. Craig, N. J. Ikin, N. Mathews, A. M. Smith, Tetrahedron Lett. 1995, 36, 7531-7534; D. Craig, A. M. Smith, Tetrahedron Lett. 1992, 33, 695-698; A. Padwa, B. H. Norman, J. Org. Chem. 1990, 55, 4801-4807; Tetrahedron Lett. 1988, 29, 3041-3044; S.-S. P. Chou, T.-M. Yuan, Synthesis 1991, 171-172; A. D. Jones, D. W. Knight J. Chem. Soc., Chem. Commun. 1996, 915-916; D. W. Knight, A. L. Redfern, J. Gilmore, Tetrahedron Lett. 1998, 39, 8909-8910.
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Recent examples of 5-endo-trig cyclizations: M. B. Berry, D. Craig, P. S. Jones, G. J. Rowlands, J. Chem. Soc., Chem. Commun. 1997, 2141-2142; D. Craig, P. S. Jones, G. J. Rowlands, Synlett 1997, 1423-1425; D. Craig, N. J. Ikin, N. Mathews, A. M. Smith, Tetrahedron Lett. 1995, 36, 7531-7534; D. Craig, A. M. Smith, Tetrahedron Lett. 1992, 33, 695-698; A. Padwa, B. H. Norman, J. Org. Chem. 1990, 55, 4801-4807; Tetrahedron Lett. 1988, 29, 3041-3044; S.-S. P. Chou, T.-M. Yuan, Synthesis 1991, 171-172; A. D. Jones, D. W. Knight J. Chem. Soc., Chem. Commun. 1996, 915-916; D. W. Knight, A. L. Redfern, J. Gilmore, Tetrahedron Lett. 1998, 39, 8909-8910.
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Recent examples of 5-endo-trig cyclizations: M. B. Berry, D. Craig, P. S. Jones, G. J. Rowlands, J. Chem. Soc., Chem. Commun. 1997, 2141-2142; D. Craig, P. S. Jones, G. J. Rowlands, Synlett 1997, 1423-1425; D. Craig, N. J. Ikin, N. Mathews, A. M. Smith, Tetrahedron Lett. 1995, 36, 7531-7534; D. Craig, A. M. Smith, Tetrahedron Lett. 1992, 33, 695-698; A. Padwa, B. H. Norman, J. Org. Chem. 1990, 55, 4801-4807; Tetrahedron Lett. 1988, 29, 3041-3044; S.-S. P. Chou, T.-M. Yuan, Synthesis 1991, 171-172; A. D. Jones, D. W. Knight J. Chem. Soc., Chem. Commun. 1996, 915-916; D. W. Knight, A. L. Redfern, J. Gilmore, Tetrahedron Lett. 1998, 39, 8909-8910.
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22
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Recent examples of 5-endo-trig cyclizations: M. B. Berry, D. Craig, P. S. Jones, G. J. Rowlands, J. Chem. Soc., Chem. Commun. 1997, 2141-2142; D. Craig, P. S. Jones, G. J. Rowlands, Synlett 1997, 1423-1425; D. Craig, N. J. Ikin, N. Mathews, A. M. Smith, Tetrahedron Lett. 1995, 36, 7531-7534; D. Craig, A. M. Smith, Tetrahedron Lett. 1992, 33, 695-698; A. Padwa, B. H. Norman, J. Org. Chem. 1990, 55, 4801-4807; Tetrahedron Lett. 1988, 29, 3041-3044; S.-S. P. Chou, T.-M. Yuan, Synthesis 1991, 171-172; A. D. Jones, D. W. Knight J. Chem. Soc., Chem. Commun. 1996, 915-916; D. W. Knight, A. L. Redfern, J. Gilmore, Tetrahedron Lett. 1998, 39, 8909-8910.
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Recent examples of 5-endo-trig cyclizations: M. B. Berry, D. Craig, P. S. Jones, G. J. Rowlands, J. Chem. Soc., Chem. Commun. 1997, 2141-2142; D. Craig, P. S. Jones, G. J. Rowlands, Synlett 1997, 1423-1425; D. Craig, N. J. Ikin, N. Mathews, A. M. Smith, Tetrahedron Lett. 1995, 36, 7531-7534; D. Craig, A. M. Smith, Tetrahedron Lett. 1992, 33, 695-698; A. Padwa, B. H. Norman, J. Org. Chem. 1990, 55, 4801-4807; Tetrahedron Lett. 1988, 29, 3041-3044; S.-S. P. Chou, T.-M. Yuan, Synthesis 1991, 171-172; A. D. Jones, D. W. Knight J. Chem. Soc., Chem. Commun. 1996, 915-916; D. W. Knight, A. L. Redfern, J. Gilmore, Tetrahedron Lett. 1998, 39, 8909-8910.
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Recent examples of 5-endo-trig cyclizations: M. B. Berry, D. Craig, P. S. Jones, G. J. Rowlands, J. Chem. Soc., Chem. Commun. 1997, 2141-2142; D. Craig, P. S. Jones, G. J. Rowlands, Synlett 1997, 1423-1425; D. Craig, N. J. Ikin, N. Mathews, A. M. Smith, Tetrahedron Lett. 1995, 36, 7531-7534; D. Craig, A. M. Smith, Tetrahedron Lett. 1992, 33, 695-698; A. Padwa, B. H. Norman, J. Org. Chem. 1990, 55, 4801-4807; Tetrahedron Lett. 1988, 29, 3041-3044; S.-S. P. Chou, T.-M. Yuan, Synthesis 1991, 171-172; A. D. Jones, D. W. Knight J. Chem. Soc., Chem. Commun. 1996, 915-916; D. W. Knight, A. L. Redfern, J. Gilmore, Tetrahedron Lett. 1998, 39, 8909-8910.
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For reviews see: A. G. M. Barrett, Chem. Soc. Rev. 1991, 20, 95-127; M. Schäfer, K. Drauz, M. Schwarm, in Houben-Weyl (Eds.: G. Helmchen, R. W. Hoffmann, J. Mulzer, E. Schaumann), Thieme, Stuttgart, 1995, vol. E21e, p 5588-5642. For recent examples see: M. A. Sturgess, D. J. Yarberry, Tetrahedron Lett. 1993, 34, 4743-4746; M. L. Morris, M. A. Sturgess, Tetrahedron Lett. 1993, 43-46; E. J. Corey, H. Estreicher, J. Am. Chem. Soc. 1978, 100, 6294-6295.
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For reviews see: A. G. M. Barrett, Chem. Soc. Rev. 1991, 20, 95-127; M. Schäfer, K. Drauz, M. Schwarm, in Houben-Weyl (Eds.: G. Helmchen, R. W. Hoffmann, J. Mulzer, E. Schaumann), Thieme, Stuttgart, 1995, vol. E21e, p 5588-5642. For recent examples see: M. A. Sturgess, D. J. Yarberry, Tetrahedron Lett. 1993, 34, 4743-4746; M. L. Morris, M. A. Sturgess, Tetrahedron Lett. 1993, 43-46; E. J. Corey, H. Estreicher, J. Am. Chem. Soc. 1978, 100, 6294-6295.
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For reviews see: A. G. M. Barrett, Chem. Soc. Rev. 1991, 20, 95-127; M. Schäfer, K. Drauz, M. Schwarm, in Houben-Weyl (Eds.: G. Helmchen, R. W. Hoffmann, J. Mulzer, E. Schaumann), Thieme, Stuttgart, 1995, vol. E21e, p 5588-5642. For recent examples see: M. A. Sturgess, D. J. Yarberry, Tetrahedron Lett. 1993, 34, 4743-4746; M. L. Morris, M. A. Sturgess, Tetrahedron Lett. 1993, 43-46; E. J. Corey, H. Estreicher, J. Am. Chem. Soc. 1978, 100, 6294-6295.
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For reviews see: A. G. M. Barrett, Chem. Soc. Rev. 1991, 20, 95-127; M. Schäfer, K. Drauz, M. Schwarm, in Houben-Weyl (Eds.: G. Helmchen, R. W. Hoffmann, J. Mulzer, E. Schaumann), Thieme, Stuttgart, 1995, vol. E21e, p 5588-5642. For recent examples see: M. A. Sturgess, D. J. Yarberry, Tetrahedron Lett. 1993, 34, 4743-4746; M. L. Morris, M. A. Sturgess, Tetrahedron Lett. 1993, 43-46; E. J. Corey, H. Estreicher, J. Am. Chem. Soc. 1978, 100, 6294-6295.
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[14a] Spartan V5.0. Wavefunction, Inc., 18401 Von Karman Avenue, Suite 370, Irvine, CA 92612, U.S.A.
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34
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0343382540
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note
-
For the 2 to 3 transformation, the following attempts met with poor results: treatment of an ether solution of 2 with diluted mineral acids or with silica gel (under magnetic stirring, in heterogeneous phase, or after adsorption to dryness), or with an organic base (DBU, pyridine, triethylamine, Hunig's base) after N-acetylation or N-tosylation of the amino group at C(3) of 2.
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36
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84921185524
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(Ed.: M. F. Grundon), Chemical Society, London
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[17b] See for example: A. R. Pinder in The Alkaloids (Ed.: M. F. Grundon), Chemical Society, London, 1982, vol. 12; J. W. Daly, T. F. Spande, in Alkaloids: Chemical and Biological Perspectives (Ed.: S. W. Pelletier), Wiley, New York, 1986, vol. 4 , chapter 1; A. B. Attygalle, E. D. Morgan, Chem. Soc. Rev. 1984, 13, 245-278; T. H. Jones, M. S. Blum, H. M. Fales, Tetrahedron 1982, 38, 1949-1958; H. Iida, N. Yamazaki, C. Kibayashi, Tetrahedron Lett. 1988, 29, 5767-5768; J. Am. Chem. Soc. 1989, 111, 1396-1408; D. H. Slee, K. L. Laslo, J. H. Elder, I. R. Ollmann, A. Gustchina, J. Kevvinen, A. Zdanov, A. Wlodawer, C.-H. Wong, J. Am. Chem. Soc. 1995, 117, 11867-11878; C. J. Andres, P. H. Lee, T. H. Nguyen, A. I. Meyers, J. Org. Chem. 1995, 60, 3189-3193 and references therein; N.-H. Lin, Y. He, H. Kopecka, Tetrahedron Lett. 1995, 36, 2563-2566.
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[17b] See for example: A. R. Pinder in The Alkaloids (Ed.: M. F. Grundon), Chemical Society, London, 1982, vol. 12; J. W. Daly, T. F. Spande, in Alkaloids: Chemical and Biological Perspectives (Ed.: S. W. Pelletier), Wiley, New York, 1986, vol. 4 , chapter 1; A. B. Attygalle, E. D. Morgan, Chem. Soc. Rev. 1984, 13, 245-278; T. H. Jones, M. S. Blum, H. M. Fales, Tetrahedron 1982, 38, 1949-1958; H. Iida, N. Yamazaki, C. Kibayashi, Tetrahedron Lett. 1988, 29, 5767-5768; J. Am. Chem. Soc. 1989, 111, 1396-1408; D. H. Slee, K. L. Laslo, J. H. Elder, I. R. Ollmann, A. Gustchina, J. Kevvinen, A. Zdanov, A. Wlodawer, C.-H. Wong, J. Am. Chem. Soc. 1995, 117, 11867-11878; C. J. Andres, P. H. Lee, T. H. Nguyen, A. I. Meyers, J. Org. Chem. 1995, 60, 3189-3193 and references therein; N.-H. Lin, Y. He, H. Kopecka, Tetrahedron Lett. 1995, 36, 2563-2566.
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