메뉴 건너뛰기




Volumn 52, Issue 35, 1996, Pages 11385-11404

Tandem radical reactions of isonitriles with 2-pyridonyl and other aryl radicals: Scope and limitations, and a first generation synthesis of (±)-camptothecin

Author keywords

[No Author keywords available]

Indexed keywords

CAMPTOTHECIN; POLYCYCLIC AROMATIC COMPOUND;

EID: 0030603102     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4020(96)00633-3     Document Type: Article
Times cited : (108)

References (69)
  • 2
    • 0000315424 scopus 로고
    • B. M. Trost and I. Fleming, Ed.; Pergamon: Oxford
    • b) Curran, D. P. In Comprehensive Organic Synthesis; B. M. Trost and I. Fleming, Ed.; Pergamon: Oxford, 1991; Vol. 4; pp 779.
    • (1991) Comprehensive Organic Synthesis , vol.4 , pp. 779
    • Curran, D.P.1
  • 9
    • 0028324328 scopus 로고
    • Selected examples appearing during 1995
    • 4. Selected examples appearing during 1995: Busato, S.; Scheffold, R. Helv. Chim. Acta 1994, 77, 92. Matzeit, A.; Schafer, H. J.; Amatore, C. Synthesis 1995, 1432. Bookermilburn, K. I.; Thompson, D. F. J. Chem. Soc., Perkin Trans. 1 1995, 2315. Bowman, W. R.; Stephenson, P. T.; Young, A. R. Tetrahedron Lett. 1995, 36, 5623. Woltering, T. J.; Hoffmann, H. M. R. Tetrahedron 1995, 51, 7389. Lopez, J. C.; Gomez, A. M.; Fraser-Reid, B. J. Org. Chem. 1995, 60, 3871. Parsons, P. J.; Penkett, C. S.; Cramp, M. C.; West, R. I.; Warrington, J.; Saraiva, M. C. Synlett 1995, 507. Zoretic, P. A.; Zhang, Y. Z.; Ribeiro, A. A. Tetrahedron Lett 1995, 36, 2929. Nishida, A.; Ogasawara, Y.; Kawahara, N.; Nishida, M. Tetrahedron Lett 1995, 36, 3015. Myers, A. G.; Condroski, K. R. J. Am. Chem. Soc. 1995, 117, 3057. Feldman, K. S. Synlett 1995, 217. Russell, G. A.; Li, C. Z.; Chen, P. J. Am. Chem. Soc. 1995, 117, 3645. Curran, D. P.; Sun, S. N. Aust. J. Chem. 1995, 48, 261.
    • (1994) Helv. Chim. Acta , vol.77 , pp. 92
    • Busato, S.1    Scheffold, R.2
  • 10
    • 0028786023 scopus 로고
    • 4. Selected examples appearing during 1995: Busato, S.; Scheffold, R. Helv. Chim. Acta 1994, 77, 92. Matzeit, A.; Schafer, H. J.; Amatore, C. Synthesis 1995, 1432. Bookermilburn, K. I.; Thompson, D. F. J. Chem. Soc., Perkin Trans. 1 1995, 2315. Bowman, W. R.; Stephenson, P. T.; Young, A. R. Tetrahedron Lett. 1995, 36, 5623. Woltering, T. J.; Hoffmann, H. M. R. Tetrahedron 1995, 51, 7389. Lopez, J. C.; Gomez, A. M.; Fraser-Reid, B. J. Org. Chem. 1995, 60, 3871. Parsons, P. J.; Penkett, C. S.; Cramp, M. C.; West, R. I.; Warrington, J.; Saraiva, M. C. Synlett 1995, 507. Zoretic, P. A.; Zhang, Y. Z.; Ribeiro, A. A. Tetrahedron Lett 1995, 36, 2929. Nishida, A.; Ogasawara, Y.; Kawahara, N.; Nishida, M. Tetrahedron Lett 1995, 36, 3015. Myers, A. G.; Condroski, K. R. J. Am. Chem. Soc. 1995, 117, 3057. Feldman, K. S. Synlett 1995, 217. Russell, G. A.; Li, C. Z.; Chen, P. J. Am. Chem. Soc. 1995, 117, 3645. Curran, D. P.; Sun, S. N. Aust. J. Chem. 1995, 48, 261.
    • (1995) Synthesis , pp. 1432
    • Matzeit, A.1    Schafer, H.J.2    Amatore, C.3
  • 11
    • 37049087515 scopus 로고
    • 4. Selected examples appearing during 1995: Busato, S.; Scheffold, R. Helv. Chim. Acta 1994, 77, 92. Matzeit, A.; Schafer, H. J.; Amatore, C. Synthesis 1995, 1432. Bookermilburn, K. I.; Thompson, D. F. J. Chem. Soc., Perkin Trans. 1 1995, 2315. Bowman, W. R.; Stephenson, P. T.; Young, A. R. Tetrahedron Lett. 1995, 36, 5623. Woltering, T. J.; Hoffmann, H. M. R. Tetrahedron 1995, 51, 7389. Lopez, J. C.; Gomez, A. M.; Fraser-Reid, B. J. Org. Chem. 1995, 60, 3871. Parsons, P. J.; Penkett, C. S.; Cramp, M. C.; West, R. I.; Warrington, J.; Saraiva, M. C. Synlett 1995, 507. Zoretic, P. A.; Zhang, Y. Z.; Ribeiro, A. A. Tetrahedron Lett 1995, 36, 2929. Nishida, A.; Ogasawara, Y.; Kawahara, N.; Nishida, M. Tetrahedron Lett 1995, 36, 3015. Myers, A. G.; Condroski, K. R. J. Am. Chem. Soc. 1995, 117, 3057. Feldman, K. S. Synlett 1995, 217. Russell, G. A.; Li, C. Z.; Chen, P. J. Am. Chem. Soc. 1995, 117, 3645. Curran, D. P.; Sun, S. N. Aust. J. Chem. 1995, 48, 261.
    • (1995) J. Chem. Soc., Perkin Trans. , vol.1 , pp. 2315
    • Bookermilburn, K.I.1    Thompson, D.F.2
  • 12
    • 0029161642 scopus 로고
    • 4. Selected examples appearing during 1995: Busato, S.; Scheffold, R. Helv. Chim. Acta 1994, 77, 92. Matzeit, A.; Schafer, H. J.; Amatore, C. Synthesis 1995, 1432. Bookermilburn, K. I.; Thompson, D. F. J. Chem. Soc., Perkin Trans. 1 1995, 2315. Bowman, W. R.; Stephenson, P. T.; Young, A. R. Tetrahedron Lett. 1995, 36, 5623. Woltering, T. J.; Hoffmann, H. M. R. Tetrahedron 1995, 51, 7389. Lopez, J. C.; Gomez, A. M.; Fraser-Reid, B. J. Org. Chem. 1995, 60, 3871. Parsons, P. J.; Penkett, C. S.; Cramp, M. C.; West, R. I.; Warrington, J.; Saraiva, M. C. Synlett 1995, 507. Zoretic, P. A.; Zhang, Y. Z.; Ribeiro, A. A. Tetrahedron Lett 1995, 36, 2929. Nishida, A.; Ogasawara, Y.; Kawahara, N.; Nishida, M. Tetrahedron Lett 1995, 36, 3015. Myers, A. G.; Condroski, K. R. J. Am. Chem. Soc. 1995, 117, 3057. Feldman, K. S. Synlett 1995, 217. Russell, G. A.; Li, C. Z.; Chen, P. J. Am. Chem. Soc. 1995, 117, 3645. Curran, D. P.; Sun, S. N. Aust. J. Chem. 1995, 48, 261.
    • (1995) Tetrahedron Lett. , vol.36 , pp. 5623
    • Bowman, W.R.1    Stephenson, P.T.2    Young, A.R.3
  • 13
    • 0029036020 scopus 로고
    • 4. Selected examples appearing during 1995: Busato, S.; Scheffold, R. Helv. Chim. Acta 1994, 77, 92. Matzeit, A.; Schafer, H. J.; Amatore, C. Synthesis 1995, 1432. Bookermilburn, K. I.; Thompson, D. F. J. Chem. Soc., Perkin Trans. 1 1995, 2315. Bowman, W. R.; Stephenson, P. T.; Young, A. R. Tetrahedron Lett. 1995, 36, 5623. Woltering, T. J.; Hoffmann, H. M. R. Tetrahedron 1995, 51, 7389. Lopez, J. C.; Gomez, A. M.; Fraser-Reid, B. J. Org. Chem. 1995, 60, 3871. Parsons, P. J.; Penkett, C. S.; Cramp, M. C.; West, R. I.; Warrington, J.; Saraiva, M. C. Synlett 1995, 507. Zoretic, P. A.; Zhang, Y. Z.; Ribeiro, A. A. Tetrahedron Lett 1995, 36, 2929. Nishida, A.; Ogasawara, Y.; Kawahara, N.; Nishida, M. Tetrahedron Lett 1995, 36, 3015. Myers, A. G.; Condroski, K. R. J. Am.Chem. Soc. 1995, 117, 3057. Feldman, K. S. Synlett 1995, 217. Russell, G. A.; Li, C. Z.; Chen, P. J. Am. Chem. Soc. 1995, 117, 3645. Curran, D. P.; Sun, S. N. Aust. J. Chem. 1995, 48, 261.
    • (1995) Tetrahedron , vol.51 , pp. 7389
    • Woltering, T.J.1    Hoffmann, H.M.R.2
  • 14
    • 0029040404 scopus 로고
    • 4. Selected examples appearing during 1995: Busato, S.; Scheffold, R. Helv. Chim. Acta 1994, 77, 92. Matzeit, A.; Schafer, H. J.; Amatore, C. Synthesis 1995, 1432. Bookermilburn, K. I.; Thompson, D. F. J. Chem. Soc., Perkin Trans. 1 1995, 2315. Bowman, W. R.; Stephenson, P. T.; Young, A. R. Tetrahedron Lett. 1995, 36, 5623. Woltering, T. J.; Hoffmann, H. M. R. Tetrahedron 1995, 51, 7389. Lopez, J. C.; Gomez, A. M.; Fraser-Reid, B. J. Org. Chem. 1995, 60, 3871. Parsons, P. J.; Penkett, C. S.; Cramp, M. C.; West, R. I.; Warrington, J.; Saraiva, M. C. Synlett 1995, 507. Zoretic, P. A.; Zhang, Y. Z.; Ribeiro, A. A. Tetrahedron Lett 1995, 36, 2929. Nishida, A.; Ogasawara, Y.; Kawahara, N.; Nishida, M. Tetrahedron Lett 1995, 36, 3015. Myers, A. G.; Condroski, K. R. J. Am. Chem. Soc. 1995, 117, 3057. Feldman, K. S. Synlett 1995, 217. Russell, G. A.; Li, C. Z.; Chen, P. J. Am. Chem. Soc. 1995, 117, 3645. Curran, D. P.; Sun, S. N. Aust. J. Chem. 1995, 48, 261.
    • (1995) J. Org. Chem. , vol.60 , pp. 3871
    • Lopez, J.C.1    Gomez, A.M.2    Fraser-Reid, B.3
  • 15
    • 0000265891 scopus 로고
    • 4. Selected examples appearing during 1995: Busato, S.; Scheffold, R. Helv. Chim. Acta 1994, 77, 92. Matzeit, A.; Schafer, H. J.; Amatore, C. Synthesis 1995, 1432. Bookermilburn, K. I.; Thompson, D. F. J. Chem. Soc., Perkin Trans. 1 1995, 2315. Bowman, W. R.; Stephenson, P. T.; Young, A. R. Tetrahedron Lett. 1995, 36, 5623. Woltering, T. J.; Hoffmann, H. M. R. Tetrahedron 1995, 51, 7389. Lopez, J. C.; Gomez, A. M.; Fraser-Reid, B. J. Org. Chem. 1995, 60, 3871. Parsons, P. J.; Penkett, C. S.; Cramp, M. C.; West, R. I.; Warrington, J.; Saraiva, M. C. Synlett 1995, 507. Zoretic, P. A.; Zhang, Y. Z.; Ribeiro, A. A. Tetrahedron Lett 1995, 36, 2929. Nishida, A.; Ogasawara, Y.; Kawahara, N.; Nishida, M. Tetrahedron Lett 1995, 36, 3015. Myers, A. G.; Condroski, K. R. J. Am. Chem. Soc. 1995, 117, 3057. Feldman, K. S. Synlett 1995, 217. Russell, G. A.; Li, C. Z.; Chen, P. J. Am. Chem. Soc. 1995, 117, 3645. Curran, D. P.; Sun, S. N. Aust. J. Chem. 1995, 48, 261.
    • (1995) Synlett , pp. 507
    • Parsons, P.J.1    Penkett, C.S.2    Cramp, M.C.3    West, R.I.4    Warrington, J.5    Saraiva, M.C.6
  • 16
    • 0028944548 scopus 로고
    • 4. Selected examples appearing during 1995: Busato, S.; Scheffold, R. Helv. Chim. Acta 1994, 77, 92. Matzeit, A.; Schafer, H. J.; Amatore, C. Synthesis 1995, 1432. Bookermilburn, K. I.; Thompson, D. F. J. Chem. Soc., Perkin Trans. 1 1995, 2315. Bowman, W. R.; Stephenson, P. T.; Young, A. R. Tetrahedron Lett. 1995, 36, 5623. Woltering, T. J.; Hoffmann, H. M. R. Tetrahedron 1995, 51, 7389. Lopez, J. C.; Gomez, A. M.; Fraser-Reid, B. J. Org. Chem. 1995, 60, 3871. Parsons, P. J.; Penkett, C. S.; Cramp, M. C.; West, R. I.; Warrington, J.; Saraiva, M. C. Synlett 1995, 507. Zoretic, P. A.; Zhang, Y. Z.; Ribeiro, A. A. Tetrahedron Lett 1995, 36, 2929. Nishida, A.; Ogasawara, Y.; Kawahara, N.; Nishida, M. Tetrahedron Lett 1995, 36, 3015. Myers, A. G.; Condroski, K. R. J. Am. Chem. Soc. 1995, 117, 3057. Feldman, K. S. Synlett 1995, 217. Russell, G. A.; Li, C. Z.; Chen, P. J. Am. Chem. Soc. 1995, 117, 3645. Curran, D. P.; Sun, S. N. Aust. J. Chem. 1995, 48, 261.
    • (1995) Tetrahedron Lett , vol.36 , pp. 2929
    • Zoretic, P.A.1    Zhang, Y.Z.2    Ribeiro, A.A.3
  • 17
    • 0028914893 scopus 로고
    • 4. Selected examples appearing during 1995: Busato, S.; Scheffold, R. Helv. Chim. Acta 1994, 77, 92. Matzeit, A.; Schafer, H. J.; Amatore, C. Synthesis 1995, 1432. Bookermilburn, K. I.; Thompson, D. F. J. Chem. Soc., Perkin Trans. 1 1995, 2315. Bowman, W. R.; Stephenson, P. T.; Young, A. R. Tetrahedron Lett. 1995, 36, 5623. Woltering, T. J.; Hoffmann, H. M. R. Tetrahedron 1995, 51, 7389. Lopez, J. C.; Gomez, A. M.; Fraser-Reid, B. J. Org. Chem. 1995, 60, 3871. Parsons, P. J.; Penkett, C. S.; Cramp, M. C.; West, R. I.; Warrington, J.; Saraiva, M. C. Synlett 1995, 507. Zoretic, P. A.; Zhang, Y. Z.; Ribeiro, A. A. Tetrahedron Lett 1995, 36, 2929. Nishida, A.; Ogasawara, Y.; Kawahara, N.; Nishida, M. Tetrahedron Lett 1995, 36, 3015. Myers, A. G.; Condroski, K. R. J. Am.Chem. Soc. 1995, 117, 3057. Feldman, K. S. Synlett 1995, 217. Russell, G. A.; Li, C. Z.; Chen, P. J. Am. Chem. Soc. 1995, 117, 3645. Curran, D. P.; Sun, S. N. Aust. J. Chem. 1995, 48, 261.
    • (1995) Tetrahedron Lett , vol.36 , pp. 3015
    • Nishida, A.1    Ogasawara, Y.2    Kawahara, N.3    Nishida, M.4
  • 18
    • 0028926001 scopus 로고
    • 4. Selected examples appearing during 1995: Busato, S.; Scheffold, R. Helv. Chim. Acta 1994, 77, 92. Matzeit, A.; Schafer, H. J.; Amatore, C. Synthesis 1995, 1432. Bookermilburn, K. I.; Thompson, D. F. J. Chem. Soc., Perkin Trans. 1 1995, 2315. Bowman, W. R.; Stephenson, P. T.; Young, A. R. Tetrahedron Lett. 1995, 36, 5623. Woltering, T. J.; Hoffmann, H. M. R. Tetrahedron 1995, 51, 7389. Lopez, J. C.; Gomez, A. M.; Fraser-Reid, B. J. Org. Chem. 1995, 60, 3871. Parsons, P. J.; Penkett, C. S.; Cramp, M. C.; West, R. I.; Warrington, J.; Saraiva, M. C. Synlett 1995, 507. Zoretic, P. A.; Zhang, Y. Z.; Ribeiro, A. A. Tetrahedron Lett 1995, 36, 2929. Nishida, A.; Ogasawara, Y.; Kawahara, N.; Nishida, M. Tetrahedron Lett 1995, 36, 3015. Myers, A. G.; Condroski, K. R. J. Am. Chem. Soc. 1995, 117, 3057. Feldman, K. S. Synlett 1995, 217. Russell, G. A.; Li, C. Z.; Chen, P. J. Am. Chem. Soc. 1995, 117, 3645. Curran, D. P.; Sun, S. N. Aust. J. Chem. 1995, 48, 261.
    • (1995) J. Am. Chem. Soc. , vol.117 , pp. 3057
    • Myers, A.G.1    Condroski, K.R.2
  • 19
    • 85064717117 scopus 로고
    • 4. Selected examples appearing during 1995: Busato, S.; Scheffold, R. Helv. Chim. Acta 1994, 77, 92. Matzeit, A.; Schafer, H. J.; Amatore, C. Synthesis 1995, 1432. Bookermilburn, K. I.; Thompson, D. F. J. Chem. Soc., Perkin Trans. 1 1995, 2315. Bowman, W. R.; Stephenson, P. T.; Young, A. R. Tetrahedron Lett. 1995, 36, 5623. Woltering, T. J.; Hoffmann, H. M. R. Tetrahedron 1995, 51, 7389. Lopez, J. C.; Gomez, A. M.; Fraser-Reid, B. J. Org. Chem. 1995, 60, 3871. Parsons, P. J.; Penkett, C. S.; Cramp, M. C.; West, R. I.; Warrington, J.; Saraiva, M. C. Synlett 1995, 507. Zoretic, P. A.; Zhang, Y. Z.; Ribeiro, A. A. Tetrahedron Lett 1995, 36, 2929. Nishida, A.; Ogasawara, Y.; Kawahara, N.; Nishida, M. Tetrahedron Lett 1995, 36, 3015. Myers, A. G.; Condroski, K. R. J. Am. Chem. Soc. 1995, 117, 3057. Feldman, K. S. Synlett 1995, 217. Russell, G. A.; Li, C. Z.; Chen, P. J. Am. Chem. Soc. 1995, 117, 3645. Curran, D. P.; Sun, S. N. Aust. J. Chem. 1995, 48, 261.
    • (1995) Synlett , pp. 217
    • Feldman, K.S.1
  • 20
    • 0000951968 scopus 로고
    • 4. Selected examples appearing during 1995: Busato, S.; Scheffold, R. Helv. Chim. Acta 1994, 77, 92. Matzeit, A.; Schafer, H. J.; Amatore, C. Synthesis 1995, 1432. Bookermilburn, K. I.; Thompson, D. F. J. Chem. Soc., Perkin Trans. 1 1995, 2315. Bowman, W. R.; Stephenson, P. T.; Young, A. R. Tetrahedron Lett. 1995, 36, 5623. Woltering, T. J.; Hoffmann, H. M. R. Tetrahedron 1995, 51, 7389. Lopez, J. C.; Gomez, A. M.; Fraser-Reid, B. J. Org. Chem. 1995, 60, 3871. Parsons, P. J.; Penkett, C. S.; Cramp, M. C.; West, R. I.; Warrington, J.; Saraiva, M. C. Synlett 1995, 507. Zoretic, P. A.; Zhang, Y. Z.; Ribeiro, A. A. Tetrahedron Lett 1995, 36, 2929. Nishida, A.; Ogasawara, Y.; Kawahara, N.; Nishida, M. Tetrahedron Lett 1995, 36, 3015. Myers, A. G.; Condroski, K. R. J. Am. Chem. Soc. 1995, 117, 3057. Feldman, K. S. Synlett 1995, 217. Russell, G. A.; Li, C. Z.; Chen, P. J. Am. Chem. Soc. 1995, 117, 3645. Curran, D. P.; Sun, S. N. Aust. J. Chem. 1995, 48, 261.
    • (1995) J. Am. Chem. Soc. , vol.117 , pp. 3645
    • Russell, G.A.1    Li, C.Z.2    Chen, P.3
  • 21
    • 84970560674 scopus 로고
    • 4. Selected examples appearing during 1995: Busato, S.; Scheffold, R. Helv. Chim. Acta 1994, 77, 92. Matzeit, A.; Schafer, H. J.; Amatore, C. Synthesis 1995, 1432. Bookermilburn, K. I.; Thompson, D. F. J. Chem. Soc., Perkin Trans. 1 1995, 2315. Bowman, W. R.; Stephenson, P. T.; Young, A. R. Tetrahedron Lett. 1995, 36, 5623. Woltering, T. J.; Hoffmann, H. M. R. Tetrahedron 1995, 51, 7389. Lopez, J. C.; Gomez, A. M.; Fraser-Reid, B. J. Org. Chem. 1995, 60, 3871. Parsons, P. J.; Penkett, C. S.; Cramp, M. C.; West, R. I.; Warrington, J.; Saraiva, M. C. Synlett 1995, 507. Zoretic, P. A.; Zhang, Y. Z.; Ribeiro, A. A. Tetrahedron Lett 1995, 36, 2929. Nishida, A.; Ogasawara, Y.; Kawahara, N.; Nishida, M. Tetrahedron Lett 1995, 36, 3015. Myers, A. G.; Condroski, K. R. J. Am. Chem. Soc. 1995, 117, 3057. Feldman, K. S. Synlett 1995, 217. Russell, G. A.; Li, C. Z.; Chen, P. J. Am. Chem. Soc. 1995, 117, 3645. Curran, D. P.; Sun, S. N. Aust. J. Chem. 1995, 48, 261.
    • (1995) Aust. J. Chem. , vol.48 , pp. 261
    • Curran, D.P.1    Sun, S.N.2
  • 45
    • 0001536923 scopus 로고
    • 3N, gave 18a in 6-10% yield
    • 3N, gave 18a in 6-10% yield. See: Cossy, J. Bull. Soc. Chim. France 1994, 131, 344.
    • (1994) Bull. Soc. Chim. France , vol.131 , pp. 344
    • Cossy, J.1
  • 54
    • 85030268227 scopus 로고
    • Ph.D. Thesis, University of Pittsburgh
    • b) Volkmann, R. A., Ph.D. Thesis, University of Pittsburgh, 1972.
    • (1972)
    • Volkmann, R.A.1
  • 65
    • 85030273468 scopus 로고    scopus 로고
    • This impurity was carried through to the radical annulation. The experiments with the chloride analog of 13a suggest that this does not participate to a significant extent in this reaction, and any remaining traces are removed by purification of the tetracycle
    • 35. This impurity was carried through to the radical annulation. The experiments with the chloride analog of 13a suggest that this does not participate to a significant extent in this reaction, and any remaining traces are removed by purification of the tetracycle.
  • 67
    • 0003377834 scopus 로고
    • Noland, W. E., Ed.; John Wiley and Sons: New York, Collect
    • 37. Gokel, G. W.; Widera, R. P.; Weber, W. P. Organic Syntheses; Noland, W. E., Ed.; John Wiley and Sons: New York, 1988; Collect. Vol. 6, p 232.
    • (1988) Organic Syntheses , vol.6 , pp. 232
    • Gokel, G.W.1    Widera, R.P.2    Weber, W.P.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.