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For a review on chromoprotein antibiotics and other enediyne natural products, see:, Eds, D. H. R. Barton, K. Nakanishi, Elsevier, Amsterdam
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For a review on chromoprotein antibiotics and other enediyne natural products, see: Z. Xi, I. H. Goldberg in Comprehensive Natural Products Chemistry, Vol. 7 (Eds.: D. H. R. Barton, K. Nakanishi), Elsevier, Amsterdam, 1999, pp.553.
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For reviews on the synthesis of enediyne compounds, see: a
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For reviews on the synthesis of enediyne compounds, see: a) K. C. Nicolaou, W.-M. Dai, Angew. Chem. 1991, 103, 1453;
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a) M. Inoue, T. Sasaki, S. Hatano, M. Hirama, Angew. Chem. 2004, 116, 6662;
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34247867982
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The total synthesis of the proposed structure of kedarcidin, a closely related enediyne chromophore, was completed recently by an elegant strategy: a F. Ren, P. C. Hogan, A. J. Anderson, A. G. Myers, J. Am. Chem. Soc. 2007, 129, 5381;
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The total synthesis of the proposed structure of kedarcidin, a closely related enediyne chromophore, was completed recently by an elegant strategy: a) F. Ren, P. C. Hogan, A. J. Anderson, A. G. Myers, J. Am. Chem. Soc. 2007, 129, 5381;
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15
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see also: b
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see also: b) A. G. Myers, A. R. Hurd, P. C. Hogan, J. Am. Chem. Soc. 2002, 124, 4583;
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c) A. G. Myers, P. C. Hogan, A. R. Hurd, S. D. Goldberg, Angew. Chem. 2002, 114, 1104;
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The phosphine-mediated elimination of thiocarbonate groups formed from cis 1,2-diols has been used to construct tenmembered-ring enediyne analogues: a M. F. Semmelhack, J. Gallagher, Tetrahedron Lett. 1993, 34, 4121;
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The phosphine-mediated elimination of thiocarbonate groups formed from cis 1,2-diols has been used to construct tenmembered-ring enediyne analogues: a) M. F. Semmelhack, J. Gallagher, Tetrahedron Lett. 1993, 34, 4121;
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19
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0032985327
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D. Crick, A. B. Pavlovic, D. J. Wink, Synth. Commun. 1999, 29, 359. However, this method was not applicable to our substrate with a trans 1,2-diol. Furthermore, the slow reaction rate is incompatible with the less stable nine-membered-ring enediyne systems.
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b) D. Crick, A. B. Pavlovic, D. J. Wink, Synth. Commun. 1999, 29, 359. However, this method was not applicable to our substrate with a trans 1,2-diol. Furthermore, the slow reaction rate is incompatible with the less stable nine-membered-ring enediyne systems.
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For recent reviews of SmI2-mediated reactions, see: a) J. M. Concellón, H. Rodríguez-Solla, Chem. Soc. Rev. 2004, 33, 599;
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24
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33947673321
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For recent examples of related reactions, see: a
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For recent examples of related reactions, see: a) J. Pospíš il, I. E. Markó, J. Am. Chem. Soc. 2007, 129, 3516;
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0029113989
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The rate of cycloaromatization of nine-membered enediyne ring systems depends on the solvent. Deuterated THF decelerated the concomitant cycloaromatization during the 1,2-elimination because of its kinetic isotope effect: K. Iida, M. Hirama, J. Am. Chem. Soc. 1995, 117, 8875; see also ref.[5].
-
The rate of cycloaromatization of nine-membered enediyne ring systems depends on the solvent. Deuterated THF decelerated the concomitant cycloaromatization during the 1,2-elimination because of its kinetic isotope effect: K. Iida, M. Hirama, J. Am. Chem. Soc. 1995, 117, 8875; see also ref.[5].
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33
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For related reactions, see: a
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For related reactions, see: a) D. P. Curran, D. Kim, H. T. Liu, W. Shen, J. Am. Chem. Soc. 1988, 110, 5900;
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b) J. W. Grissom, D. Klingberg, S. Meyenburg, B. L. Stallman, J. Org. Chem. 1994, 59, 7876;
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36448956880
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The total synthesis of the maduropeptin aglycon was carried out by using the present strategy: K. Komano, S. Shimamura, M. Inoue, M. Hirama, J. Am. Chem. Soc. 2007, 129, 14184.
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The total synthesis of the maduropeptin aglycon was carried out by using the present strategy: K. Komano, S. Shimamura, M. Inoue, M. Hirama, J. Am. Chem. Soc. 2007, 129, 14184.
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