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Volumn 43, Issue 47, 2004, Pages 6500-6505

Synthesis of the C-1027 chromophore framework through atropselective macrolactonization

Author keywords

Alkynes; Antitumor agents; Atropisomerism; Lactones; Macrocycles

Indexed keywords

ADDITION REACTIONS; ALDEHYDES; LITHIUM COMPOUNDS; SYNTHESIS (CHEMICAL);

EID: 11144303387     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200461428     Document Type: Article
Times cited : (37)

References (61)
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    • Total syntheses of the nine-membered ring enediynes were reported: N-1999A2: a) S. Kobayashi, S. Ashizawa, Y. Takahashi, Y. Sugiura, M. Nagaoka, M. J. Lear, M. Hirama, J. Am. Chem. Soc. 2001, 123, 11294-11295; neocarzinostatin chromophore: b) A. G. Myers, J. Liang, M. Hammond, P. M. Harrington, Y. Wu, E, Y. Kuo, J. Am. Chem. Soc. 1998, 120, 5319-5320; c) A. G. Myers, R. Glatthar, M. Hammond, P. M. Harrington, E, Y. Kuo, J. Liang, S. E. Schaus, Y. Wu, J.-N. Xiang, J. Am. Chem. Soc. 2002, 124, 5380-5401.
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    • Total syntheses of the nine-membered ring enediynes were reported: N-1999A2: a) S. Kobayashi, S. Ashizawa, Y. Takahashi, Y. Sugiura, M. Nagaoka, M. J. Lear, M. Hirama, J. Am. Chem. Soc. 2001, 123, 11294-11295; neocarzinostatin chromophore: b) A. G. Myers, J. Liang, M. Hammond, P. M. Harrington, Y. Wu, E, Y. Kuo, J. Am. Chem. Soc. 1998, 120, 5319-5320; c) A. G. Myers, R. Glatthar, M. Hammond, P. M. Harrington, E, Y. Kuo, J. Liang, S. E. Schaus, Y. Wu, J.-N. Xiang, J. Am. Chem. Soc. 2002, 124, 5380-5401.
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    • Myers, A.G.1    Glatthar, R.2    Hammond, M.3    Harrington, P.M.4    Kuo, E.Y.5    Liang, J.6    Schaus, S.E.7    Wu, Y.8    Xiang, J.-N.9
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    • For recent synthetic studies of the enediyne natural products from this laboratory, see: neocarzinostatin chromophore: a) K. Toyama, S. Iguchi, H. Sakazaki, T. Oishi, M. Hirama, Bull. Chem. Soc. Jpn. 2001, 74, 997-1008; kedarcidin: b) F. Yoshimura, S. Kawata, M. Hirama, Tetrahedron Lett. 1999, 40, 8281-8285; c) I. Ohashi, M. J. Lear, F. Yoshimura, M. Hirama, Org. Lett. 2004, 6, 719-722; maduropeptin: d) N. Kato, S. Shimamura, Y. Kikai, M. Hirama, Synlett 2004, 2107-2110, and references therein.
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    • 0033584943 scopus 로고    scopus 로고
    • For recent synthetic studies of the enediyne natural products from this laboratory, see: neocarzinostatin chromophore: a) K. Toyama, S. Iguchi, H. Sakazaki, T. Oishi, M. Hirama, Bull. Chem. Soc. Jpn. 2001, 74, 997-1008; kedarcidin: b) F. Yoshimura, S. Kawata, M. Hirama, Tetrahedron Lett. 1999, 40, 8281-8285; c) I. Ohashi, M. J. Lear, F. Yoshimura, M. Hirama, Org. Lett. 2004, 6, 719-722; maduropeptin: d) N. Kato, S. Shimamura, Y. Kikai, M. Hirama, Synlett 2004, 2107-2110, and references therein.
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    • 1642383551 scopus 로고    scopus 로고
    • For recent synthetic studies of the enediyne natural products from this laboratory, see: neocarzinostatin chromophore: a) K. Toyama, S. Iguchi, H. Sakazaki, T. Oishi, M. Hirama, Bull. Chem. Soc. Jpn. 2001, 74, 997-1008; kedarcidin: b) F. Yoshimura, S. Kawata, M. Hirama, Tetrahedron Lett. 1999, 40, 8281-8285; c) I. Ohashi, M. J. Lear, F. Yoshimura, M. Hirama, Org. Lett. 2004, 6, 719-722; maduropeptin: d) N. Kato, S. Shimamura, Y. Kikai, M. Hirama, Synlett 2004, 2107-2110, and references therein.
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    • 5644251929 scopus 로고    scopus 로고
    • and references therein
    • For recent synthetic studies of the enediyne natural products from this laboratory, see: neocarzinostatin chromophore: a) K. Toyama, S. Iguchi, H. Sakazaki, T. Oishi, M. Hirama, Bull. Chem. Soc. Jpn. 2001, 74, 997-1008; kedarcidin: b) F. Yoshimura, S. Kawata, M. Hirama, Tetrahedron Lett. 1999, 40, 8281-8285; c) I. Ohashi, M. J. Lear, F. Yoshimura, M. Hirama, Org. Lett. 2004, 6, 719-722; maduropeptin: d) N. Kato, S. Shimamura, Y. Kikai, M. Hirama, Synlett 2004, 2107-2110, and references therein.
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    • Kato, N.1    Shimamura, S.2    Kikai, Y.3    Hirama, M.4
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    • For the synthesis of the protected kedarcidin chromophore aglycon, see: A. G. Myers, P. C. Hogan, A. R. Hurd, S. D. Goldberg, Angew. Chem. 2002, 114, 1104-1109; Angew. Chem. Int. Ed. 2002, 41, 1062-1066.
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    • Myers, A.G.1    Hogan, P.C.2    Hurd, A.R.3    Goldberg, S.D.4
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    • 0037087618 scopus 로고    scopus 로고
    • For the synthesis of the protected kedarcidin chromophore aglycon, see: A. G. Myers, P. C. Hogan, A. R. Hurd, S. D. Goldberg, Angew. Chem. 2002, 114, 1104-1109; Angew. Chem. Int. Ed. 2002, 41, 1062-1066.
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    • Only a few examples have been reported on the stereoselective synthesis of nonbiaryl stereogenic axes in natural product syntheses; see: a) D. A. Evans, M. R. Wood, B. W. Trotter, T. I. Richardson, J. C. Barrow, J. L. Katz, Angew. Chem. 1998, 110, 2864-2868; Angew. Chem. Int. Ed. 1998, 37, 2700-2703; b) D. A. Evans, C. J. Dinsmore, P. S. Watson, M. R. Wood, T. I. Richardson, B. W. Trotter, J. L. Katz, Angew. Chem. 1998, 110, 2868-2872; Angew. Chem. Int. Ed. 1998, 37, 2704-2708; c) M. E. Layton, C. A. Morales, M. D. Shair, J. Am. Chem. Soc. 2002, 124, 773-775; d) K. C. Nicolaou, C. N. C. Boddy, J. Am. Chem. Soc. 2002, 124, 10451-10455; see also references [9b] and [10].
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    • Evans, D.A.1    Wood, M.R.2    Trotter, B.W.3    Richardson, T.I.4    Barrow, J.C.5    Katz, J.L.6
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    • 0032538575 scopus 로고    scopus 로고
    • Only a few examples have been reported on the stereoselective synthesis of nonbiaryl stereogenic axes in natural product syntheses; see: a) D. A. Evans, M. R. Wood, B. W. Trotter, T. I. Richardson, J. C. Barrow, J. L. Katz, Angew. Chem. 1998, 110, 2864-2868; Angew. Chem. Int. Ed. 1998, 37, 2700-2703; b) D. A. Evans, C. J. Dinsmore, P. S. Watson, M. R. Wood, T. I. Richardson, B. W. Trotter, J. L. Katz, Angew. Chem. 1998, 110, 2868-2872; Angew. Chem. Int. Ed. 1998, 37, 2704-2708; c) M. E. Layton, C. A. Morales, M. D. Shair, J. Am. Chem. Soc. 2002, 124, 773-775; d) K. C. Nicolaou, C. N. C. Boddy, J. Am. Chem. Soc. 2002, 124, 10451-10455; see also references [9b] and [10].
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  • 32
    • 0001525716 scopus 로고    scopus 로고
    • Only a few examples have been reported on the stereoselective synthesis of nonbiaryl stereogenic axes in natural product syntheses; see: a) D. A. Evans, M. R. Wood, B. W. Trotter, T. I. Richardson, J. C. Barrow, J. L. Katz, Angew. Chem. 1998, 110, 2864-2868; Angew. Chem. Int. Ed. 1998, 37, 2700-2703; b) D. A. Evans, C. J. Dinsmore, P. S. Watson, M. R. Wood, T. I. Richardson, B. W. Trotter, J. L. Katz, Angew. Chem. 1998, 110, 2868-2872; Angew. Chem. Int. Ed. 1998, 37, 2704-2708; c) M. E. Layton, C. A. Morales, M. D. Shair, J. Am. Chem. Soc. 2002, 124, 773-775; d) K. C. Nicolaou, C. N. C. Boddy, J. Am. Chem. Soc. 2002, 124, 10451-10455; see also references [9b] and [10].
    • (1998) Angew. Chem. , vol.110 , pp. 2868-2872
    • Evans, D.A.1    Dinsmore, C.J.2    Watson, P.S.3    Wood, M.R.4    Richardson, T.I.5    Trotter, B.W.6    Katz, J.L.7
  • 33
    • 0032538360 scopus 로고    scopus 로고
    • Only a few examples have been reported on the stereoselective synthesis of nonbiaryl stereogenic axes in natural product syntheses; see: a) D. A. Evans, M. R. Wood, B. W. Trotter, T. I. Richardson, J. C. Barrow, J. L. Katz, Angew. Chem. 1998, 110, 2864-2868; Angew. Chem. Int. Ed. 1998, 37, 2700-2703; b) D. A. Evans, C. J. Dinsmore, P. S. Watson, M. R. Wood, T. I. Richardson, B. W. Trotter, J. L. Katz, Angew. Chem. 1998, 110, 2868-2872; Angew. Chem. Int. Ed. 1998, 37, 2704-2708; c) M. E. Layton, C. A. Morales, M. D. Shair, J. Am. Chem. Soc. 2002, 124, 773-775; d) K. C. Nicolaou, C. N. C. Boddy, J. Am. Chem. Soc. 2002, 124, 10451-10455; see also references [9b] and [10].
    • (1998) Angew. Chem. Int. Ed. , vol.37 , pp. 2704-2708
  • 34
    • 0037028571 scopus 로고    scopus 로고
    • Only a few examples have been reported on the stereoselective synthesis of nonbiaryl stereogenic axes in natural product syntheses; see: a) D. A. Evans, M. R. Wood, B. W. Trotter, T. I. Richardson, J. C. Barrow, J. L. Katz, Angew. Chem. 1998, 110, 2864-2868; Angew. Chem. Int. Ed. 1998, 37, 2700-2703; b) D. A. Evans, C. J. Dinsmore, P. S. Watson, M. R. Wood, T. I. Richardson, B. W. Trotter, J. L. Katz, Angew. Chem. 1998, 110, 2868-2872; Angew. Chem. Int. Ed. 1998, 37, 2704-2708; c) M. E. Layton, C. A. Morales, M. D. Shair, J. Am. Chem. Soc. 2002, 124, 773-775; d) K. C. Nicolaou, C. N. C. Boddy, J. Am. Chem. Soc. 2002, 124, 10451-10455; see also references [9b] and [10].
    • (2002) J. Am. Chem. Soc. , vol.124 , pp. 773-775
    • Layton, M.E.1    Morales, C.A.2    Shair, M.D.3
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    • see also references [9b] and [10]
    • Only a few examples have been reported on the stereoselective synthesis of nonbiaryl stereogenic axes in natural product syntheses; see: a) D. A. Evans, M. R. Wood, B. W. Trotter, T. I. Richardson, J. C. Barrow, J. L. Katz, Angew. Chem. 1998, 110, 2864-2868; Angew. Chem. Int. Ed. 1998, 37, 2700-2703; b) D. A. Evans, C. J. Dinsmore, P. S. Watson, M. R. Wood, T. I. Richardson, B. W. Trotter, J. L. Katz, Angew. Chem. 1998, 110, 2868-2872; Angew. Chem. Int. Ed. 1998, 37, 2704-2708; c) M. E. Layton, C. A. Morales, M. D. Shair, J. Am. Chem. Soc. 2002, 124, 773-775; d) K. C. Nicolaou, C. N. C. Boddy, J. Am. Chem. Soc. 2002, 124, 10451-10455; see also references [9b] and [10].
    • (2002) J. Am. Chem. Soc. , vol.124 , pp. 10451-10455
    • Nicolaou, K.C.1    Boddy, C.N.C.2
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    • For other studies on bicyclo[7.3.0]dodecadiyne formation, see: a) P. A. Wender, M. Harmata, D. Jeffery, C. Mukai, J. Suffert, Tetrahedron Lett. 1988, 29, 909-912; b) P. A. Wender, J. A. McKinney, C. Mukai, J. Am. Chem. Soc. 1990, 112, 5369-5370; c) T. Doi, T. Takahashi, J. Org. Chem. 1991, 56, 3465-3467; d) P. Magnus, R. Carter, M. Davies, J. Elliott, T. Pitterna, Tetrahedron 1996, 52, 6283-6306; e) H. Tanaka, H. Yamada, A. Matsuda, T. Takahashi, Synlett 1997, 381-383; f) S. Caddick, V. M. Delisser, V. E. Doyle, S. Khan, A. G. Avent, S. Vile, Tetrahedron 1999, 55, 2737-2754, and references therein.
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    • For other studies on bicyclo[7.3.0]dodecadiyne formation, see: a) P. A. Wender, M. Harmata, D. Jeffery, C. Mukai, J. Suffert, Tetrahedron Lett. 1988, 29, 909-912; b) P. A. Wender, J. A. McKinney, C. Mukai, J. Am. Chem. Soc. 1990, 112, 5369-5370; c) T. Doi, T. Takahashi, J. Org. Chem. 1991, 56, 3465-3467; d) P. Magnus, R. Carter, M. Davies, J. Elliott, T. Pitterna, Tetrahedron 1996, 52, 6283-6306; e) H. Tanaka, H. Yamada, A. Matsuda, T. Takahashi, Synlett 1997, 381-383; f) S. Caddick, V. M. Delisser, V. E. Doyle, S. Khan, A. G. Avent, S. Vile, Tetrahedron 1999, 55, 2737-2754, and references therein.
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    • For other studies on bicyclo[7.3.0]dodecadiyne formation, see: a) P. A. Wender, M. Harmata, D. Jeffery, C. Mukai, J. Suffert, Tetrahedron Lett. 1988, 29, 909-912; b) P. A. Wender, J. A. McKinney, C. Mukai, J. Am. Chem. Soc. 1990, 112, 5369-5370; c) T. Doi, T. Takahashi, J. Org. Chem. 1991, 56, 3465-3467; d) P. Magnus, R. Carter, M. Davies, J. Elliott, T. Pitterna, Tetrahedron 1996, 52, 6283-6306; e) H. Tanaka, H. Yamada, A. Matsuda, T. Takahashi, Synlett 1997, 381-383; f) S. Caddick, V. M. Delisser, V. E. Doyle, S. Khan, A. G. Avent, S. Vile, Tetrahedron 1999, 55, 2737-2754, and references therein.
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    • For other studies on bicyclo[7.3.0]dodecadiyne formation, see: a) P. A. Wender, M. Harmata, D. Jeffery, C. Mukai, J. Suffert, Tetrahedron Lett. 1988, 29, 909-912; b) P. A. Wender, J. A. McKinney, C. Mukai, J. Am. Chem. Soc. 1990, 112, 5369-5370; c) T. Doi, T. Takahashi, J. Org. Chem. 1991, 56, 3465-3467; d) P. Magnus, R. Carter, M. Davies, J. Elliott, T. Pitterna, Tetrahedron 1996, 52, 6283-6306; e) H. Tanaka, H. Yamada, A. Matsuda, T. Takahashi, Synlett 1997, 381-383; f) S. Caddick, V. M. Delisser, V. E. Doyle, S. Khan, A. G. Avent, S. Vile, Tetrahedron 1999, 55, 2737-2754, and references therein.
    • (1997) Synlett , pp. 381-383
    • Tanaka, H.1    Yamada, H.2    Matsuda, A.3    Takahashi, T.4
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    • and references therein
    • For other studies on bicyclo[7.3.0]dodecadiyne formation, see: a) P. A. Wender, M. Harmata, D. Jeffery, C. Mukai, J. Suffert, Tetrahedron Lett. 1988, 29, 909-912; b) P. A. Wender, J. A. McKinney, C. Mukai, J. Am. Chem. Soc. 1990, 112, 5369-5370; c) T. Doi, T. Takahashi, J. Org. Chem. 1991, 56, 3465-3467; d) P. Magnus, R. Carter, M. Davies, J. Elliott, T. Pitterna, Tetrahedron 1996, 52, 6283-6306; e) H. Tanaka, H. Yamada, A. Matsuda, T. Takahashi, Synlett 1997, 381-383; f) S. Caddick, V. M. Delisser, V. E. Doyle, S. Khan, A. G. Avent, S. Vile, Tetrahedron 1999, 55, 2737-2754, and references therein.
    • (1999) Tetrahedron , vol.55 , pp. 2737-2754
    • Caddick, S.1    Delisser, V.M.2    Doyle, V.E.3    Khan, S.4    Avent, A.G.5    Vile, S.6
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    • Interestingly, the facile atropisomerism of kedarcidin synthetic intermediates has been observed: A. G. Myers, A. R. Hurd, P. C. Hogan, J. Am. Chem. Soc. 2002, 124, 4583-4585. see also reference [10].
    • (2002) J. Am. Chem. Soc. , vol.124 , pp. 4583-4585
    • Myers, A.G.1    Hurd, A.R.2    Hogan, P.C.3
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