Efficient construction of the kedarcidin chromophore ansamacrolide

Organic Letters

Volumn 7, Issue 2, 2005, Pages 267-270

  Koyama, Yasuhito ^a   Lear, Martin J ^a,b   Yoshimura, Fumihiko ^a   Ohashi, Isao ^a   Mashimo, Tomoko ^a   Hirama, Masahiro ^a  

^a TOHOKU UNIVERSITY   (Japan)

^b NATIONAL UNIVERSITY OF SINGAPORE   (Singapore)

Author keywords

[No Author keywords available]

Indexed keywords

CHLORINE DERIVATIVE; CYCLOPENTENE DERIVATIVE; EPOXIDE; KEDARCIDIN; KETONE; MACROLIDE;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHROMATOPHORE; SONOGASHIRA REACTION; SUBSTITUTION REACTION; SYNTHESIS;

EID: 13444263558     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0477374     Document Type: Article

References (40)

1. Isolation of kedarcidin and chromophore structure (1): (a) Lam, K. S.; Hesler, G. A.; Gustavson, D. R.; Crosswell, A. R.; Veitch, J. M.; Forenza, S.; Tomita, K. J. Antibiot. 1991, 44, 472. Hofstead, S. J.; Matson, J. A.; Malacko, A. R.; Marquardt, H. J. Antibiot. 1992, 45, 1250. (b) Leet, J. E.; Schroeder, D. R.; Langley, D. R.; Colson K. L.; Huang, S.; Klohr, S. E.; Lee, M. S.; Golik, J.; Hofstead, S. J.; Doyle, T. W.; Matson, J. A. J. Am. Chem. Soc. 1993, 115, 8432. (c) Structure revision and synthesis of fragments 5 and 7: Kawata, S.; Ashizawa, S.; Hirama, M. J. Am. Chem. Soc. 1997, 119, 12012.
2. Isolation of kedarcidin and chromophore structure (1): (a) Lam, K. S.; Hesler, G. A.; Gustavson, D. R.; Crosswell, A. R.; Veitch, J. M.; Forenza, S.; Tomita, K. J. Antibiot. 1991, 44, 472. Hofstead, S. J.; Matson, J. A.; Malacko, A. R.; Marquardt, H. J. Antibiot. 1992, 45, 1250. (b) Leet, J. E.; Schroeder, D. R.; Langley, D. R.; Colson K. L.; Huang, S.; Klohr, S. E.; Lee, M. S.; Golik, J.; Hofstead, S. J.; Doyle, T. W.; Matson, J. A. J. Am. Chem. Soc. 1993, 115, 8432. (c) Structure revision and synthesis of fragments 5 and 7: Kawata, S.; Ashizawa, S.; Hirama, M. J. Am. Chem. Soc. 1997, 119, 12012.
3. Isolation of kedarcidin and chromophore structure (1): (a) Lam, K. S.; Hesler, G. A.; Gustavson, D. R.; Crosswell, A. R.; Veitch, J. M.; Forenza, S.; Tomita, K. J. Antibiot. 1991, 44, 472. Hofstead, S. J.; Matson, J. A.; Malacko, A. R.; Marquardt, H. J. Antibiot. 1992, 45, 1250. (b) Leet, J. E.; Schroeder, D. R.; Langley, D. R.; Colson K. L.; Huang, S.; Klohr, S. E.; Lee, M. S.; Golik, J.; Hofstead, S. J.; Doyle, T. W.; Matson, J. A. J. Am. Chem. Soc. 1993, 115, 8432. (c) Structure revision and synthesis of fragments 5 and 7: Kawata, S.; Ashizawa, S.; Hirama, M. J. Am. Chem. Soc. 1997, 119, 12012.
4. Isolation of kedarcidin and chromophore structure (1): (a) Lam, K. S.; Hesler, G. A.; Gustavson, D. R.; Crosswell, A. R.; Veitch, J. M.; Forenza, S.; Tomita, K. J. Antibiot. 1991, 44, 472. Hofstead, S. J.; Matson, J. A.; Malacko, A. R.; Marquardt, H. J. Antibiot. 1992, 45, 1250. (b) Leet, J. E.; Schroeder, D. R.; Langley, D. R.; Colson K. L.; Huang, S.; Klohr, S. E.; Lee, M. S.; Golik, J.; Hofstead, S. J.; Doyle, T. W.; Matson, J. A. J. Am. Chem. Soc. 1993, 115, 8432. (c) Structure revision and synthesis of fragments 5 and 7: Kawata, S.; Ashizawa, S.; Hirama, M. J. Am. Chem. Soc. 1997, 119, 12012.
5. Myers, A. G.; Hogan, P. C.; Hurd, A. R.; Goldberg, S. D. Angew. Chem., Int. Ed. 2002, 41, 1062.
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9. Examples in advanced synthetic settings: (a) Kawata, S.; Yoshimura, F.; Irie, J.; Ehara, H.; Hirama, M. Synlett 1997, 250. (b) Kobayashi, S.; Ashizawa, S.; Takahashi, Y.; Suigura, Y.; Nagaoka, M.; Lear, M. J.; Hirama, M. J. Am. Chem. Soc. 2001, 123, 11294. (c) Das, P.; Mita, T.; Lear, M. J.; Hirama, M. Chem. Commun. 2002, 2624. (d) Inoue, M.; Kikuchi, T.; Hirama, M. Tetrahedron Lett. 2004, 45, 6439. (e) Inoue, M.; Sasaki, T.; Hatano, S.; Hirama, M. Angew. Chem., Int. Ed. 2004, 43, 6500.
10. Examples in advanced synthetic settings: (a) Kawata, S.; Yoshimura, F.; Irie, J.; Ehara, H.; Hirama, M. Synlett 1997, 250. (b) Kobayashi, S.; Ashizawa, S.; Takahashi, Y.; Suigura, Y.; Nagaoka, M.; Lear, M. J.; Hirama, M. J. Am. Chem. Soc. 2001, 123, 11294. (c) Das, P.; Mita, T.; Lear, M. J.; Hirama, M. Chem. Commun. 2002, 2624. (d) Inoue, M.; Kikuchi, T.; Hirama, M. Tetrahedron Lett. 2004, 45, 6439. (e) Inoue, M.; Sasaki, T.; Hatano, S.; Hirama, M. Angew. Chem., Int. Ed. 2004, 43, 6500.
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12. Examples in advanced synthetic settings: (a) Kawata, S.; Yoshimura, F.; Irie, J.; Ehara, H.; Hirama, M. Synlett 1997, 250. (b) Kobayashi, S.; Ashizawa, S.; Takahashi, Y.; Suigura, Y.; Nagaoka, M.; Lear, M. J.; Hirama, M. J. Am. Chem. Soc. 2001, 123, 11294. (c) Das, P.; Mita, T.; Lear, M. J.; Hirama, M. Chem. Commun. 2002, 2624. (d) Inoue, M.; Kikuchi, T.; Hirama, M. Tetrahedron Lett. 2004, 45, 6439. (e) Inoue, M.; Sasaki, T.; Hatano, S.; Hirama, M. Angew. Chem., Int. Ed. 2004, 43, 6500.
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