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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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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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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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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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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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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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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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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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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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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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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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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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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.
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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 an excellent example of the selective isomerization of atropisomers in the context of a total synthesis of vancomycin, see: D. L. Boger, S. Miyazaki, S. H. Kim, J. H. Wu, S. L. Castle, O. Loiseleur, Q. Jin, J. Am. Chem. Soc. 1999, 121, 10004-10011.
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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].
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Yamaguchi lactonization of 31 gave 32 in lower yield (32: 33%, 33: 6%, dimer: 30%); J. Inanaga, K. Hirata, H. Saeki, T. Katsuki, M. Yamaguchi, Bull. Chem. Soc. Jpn. 1979, 52, 1989-1993.
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11144331609
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note
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[19b]
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61
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11144261108
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note
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[18]
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