A new convergent approach to the polycyclic framework of dynemicin A

Journal of Organic Chemistry

Volumn 62, Issue 10, 1997, Pages 3028-3029

  Escudero, Sonia ^a   Pérez, Dolores ^a   Guitián, Enrique ^a   Castedo, Luis ^a  

^a UNIVERSITY OF SANTIAGO DE COMPOSTELA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIBIOTIC AGENT; DYNEMICIN A;

ARTICLE; DRUG SYNTHESIS; IN VITRO STUDY; REACTION ANALYSIS;

EID: 0030941923     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9702047     Document Type: Article

References (20)

1. (a) Konishi, M.; Ohkuma, H.; Matsumoto, K.; Tsuno, T.; Kamei, H.; Miyaki, T.; Oki, T.; Kawaguchi, H.; VanDuyne, G. D.; Clardy, J. J. Antibiot. 1989, 42, 1449.
2. (b) Konishi, M.; Ohkuma, H.; Tsuno, T.; Oki, T.; VanDuyne, G. D.; Clardy, J. J. Am. Chem. Soc. 1990, 112, 3715.
3. For selected references on the synthesis of dynemicin A and model systems, see: (a) Danishefsky, S. J.; Shair, M. D. J. Org. Chem. 1996, 61, 16. (b) Shair, M. D., Yoon, T.-Y.; Danishefsky, S. J. Angew. Chem., Int. Ed. Engl. 1995, 34, 1721. (c) Takahashi, T.; Sakamoto, Y.; Yamada, H.; Usui, S.; Fukazawa, Y. Angew. Chem., Int. Ed. Engl. 1995, 34, 1345. (d) Nishikawa, T.; Ino, A.; Isobe, M. Tetrahedron 1994, 50, 1449. (e) Taunton, J.; Wood, J. L.; Schreiber, S. L. J. Am. Chem. Soc. 1993, 115, 10378. (f) Nicolaou, K. C.; Dai, W.-M.; Hong, Y. P.; Tsay, S. C.; Baldridge, K. K.; Siegel, J. S. J. Am. Chem. Soc. 1993, 115, 7944. (g) Wender, P. A.; Zercher, C. K.; Beckham, S.; Haubold, E.-M. J. Org. Chem. 1993, 58, 5867.
4. For selected references on the synthesis of dynemicin A and model systems, see: (a) Danishefsky, S. J.; Shair, M. D. J. Org. Chem. 1996, 61, 16. (b) Shair, M. D., Yoon, T.-Y.; Danishefsky, S. J. Angew. Chem., Int. Ed. Engl. 1995, 34, 1721. (c) Takahashi, T.; Sakamoto, Y.; Yamada, H.; Usui, S.; Fukazawa, Y. Angew. Chem., Int. Ed. Engl. 1995, 34, 1345. (d) Nishikawa, T.; Ino, A.; Isobe, M. Tetrahedron 1994, 50, 1449. (e) Taunton, J.; Wood, J. L.; Schreiber, S. L. J. Am. Chem. Soc. 1993, 115, 10378. (f) Nicolaou, K. C.; Dai, W.-M.; Hong, Y. P.; Tsay, S. C.; Baldridge, K. K.; Siegel, J. S. J. Am. Chem. Soc. 1993, 115, 7944. (g) Wender, P. A.; Zercher, C. K.; Beckham, S.; Haubold, E.-M. J. Org. Chem. 1993, 58, 5867.
5. For selected references on the synthesis of dynemicin A and model systems, see: (a) Danishefsky, S. J.; Shair, M. D. J. Org. Chem. 1996, 61, 16. (b) Shair, M. D., Yoon, T.-Y.; Danishefsky, S. J. Angew. Chem., Int. Ed. Engl. 1995, 34, 1721. (c) Takahashi, T.; Sakamoto, Y.; Yamada, H.; Usui, S.; Fukazawa, Y. Angew. Chem., Int. Ed. Engl. 1995, 34, 1345. (d) Nishikawa, T.; Ino, A.; Isobe, M. Tetrahedron 1994, 50, 1449. (e) Taunton, J.; Wood, J. L.; Schreiber, S. L. J. Am. Chem. Soc. 1993, 115, 10378. (f) Nicolaou, K. C.; Dai, W.-M.; Hong, Y. P.; Tsay, S. C.; Baldridge, K. K.; Siegel, J. S. J. Am. Chem. Soc. 1993, 115, 7944. (g) Wender, P. A.; Zercher, C. K.; Beckham, S.; Haubold, E.-M. J. Org. Chem. 1993, 58, 5867.
6. For selected references on the synthesis of dynemicin A and model systems, see: (a) Danishefsky, S. J.; Shair, M. D. J. Org. Chem. 1996, 61, 16. (b) Shair, M. D., Yoon, T.-Y.; Danishefsky, S. J. Angew. Chem., Int. Ed. Engl. 1995, 34, 1721. (c) Takahashi, T.; Sakamoto, Y.; Yamada, H.; Usui, S.; Fukazawa, Y. Angew. Chem., Int. Ed. Engl. 1995, 34, 1345. (d) Nishikawa, T.; Ino, A.; Isobe, M. Tetrahedron 1994, 50, 1449. (e) Taunton, J.; Wood, J. L.; Schreiber, S. L. J. Am. Chem. Soc. 1993, 115, 10378. (f) Nicolaou, K. C.; Dai, W.-M.; Hong, Y. P.; Tsay, S. C.; Baldridge, K. K.; Siegel, J. S. J. Am. Chem. Soc. 1993, 115, 7944. (g) Wender, P. A.; Zercher, C. K.; Beckham, S.; Haubold, E.-M. J. Org. Chem. 1993, 58, 5867.
7. For selected references on the synthesis of dynemicin A and model systems, see: (a) Danishefsky, S. J.; Shair, M. D. J. Org. Chem. 1996, 61, 16. (b) Shair, M. D., Yoon, T.-Y.; Danishefsky, S. J. Angew. Chem., Int. Ed. Engl. 1995, 34, 1721. (c) Takahashi, T.; Sakamoto, Y.; Yamada, H.; Usui, S.; Fukazawa, Y. Angew. Chem., Int. Ed. Engl. 1995, 34, 1345. (d) Nishikawa, T.; Ino, A.; Isobe, M. Tetrahedron 1994, 50, 1449. (e) Taunton, J.; Wood, J. L.; Schreiber, S. L. J. Am. Chem. Soc. 1993, 115, 10378. (f) Nicolaou, K. C.; Dai, W.-M.; Hong, Y. P.; Tsay, S. C.; Baldridge, K. K.; Siegel, J. S. J. Am. Chem. Soc. 1993, 115, 7944. (g) Wender, P. A.; Zercher, C. K.; Beckham, S.; Haubold, E.-M. J. Org. Chem. 1993, 58, 5867.
8. For selected references on the synthesis of dynemicin A and model systems, see: (a) Danishefsky, S. J.; Shair, M. D. J. Org. Chem. 1996, 61, 16. (b) Shair, M. D., Yoon, T.-Y.; Danishefsky, S. J. Angew. Chem., Int. Ed. Engl. 1995, 34, 1721. (c) Takahashi, T.; Sakamoto, Y.; Yamada, H.; Usui, S.; Fukazawa, Y. Angew. Chem., Int. Ed. Engl. 1995, 34, 1345. (d) Nishikawa, T.; Ino, A.; Isobe, M. Tetrahedron 1994, 50, 1449. (e) Taunton, J.; Wood, J. L.; Schreiber, S. L. J. Am. Chem. Soc. 1993, 115, 10378. (f) Nicolaou, K. C.; Dai, W.-M.; Hong, Y. P.; Tsay, S. C.; Baldridge, K. K.; Siegel, J. S. J. Am. Chem. Soc. 1993, 115, 7944. (g) Wender, P. A.; Zercher, C. K.; Beckham, S.; Haubold, E.-M. J. Org. Chem. 1993, 58, 5867.
9. For selected references on the synthesis of dynemicin A and model systems, see: (a) Danishefsky, S. J.; Shair, M. D. J. Org. Chem. 1996, 61, 16. (b) Shair, M. D., Yoon, T.-Y.; Danishefsky, S. J. Angew. Chem., Int. Ed. Engl. 1995, 34, 1721. (c) Takahashi, T.; Sakamoto, Y.; Yamada, H.; Usui, S.; Fukazawa, Y. Angew. Chem., Int. Ed. Engl. 1995, 34, 1345. (d) Nishikawa, T.; Ino, A.; Isobe, M. Tetrahedron 1994, 50, 1449. (e) Taunton, J.; Wood, J. L.; Schreiber, S. L. J. Am. Chem. Soc. 1993, 115, 10378. (f) Nicolaou, K. C.; Dai, W.-M.; Hong, Y. P.; Tsay, S. C.; Baldridge, K. K.; Siegel, J. S. J. Am. Chem. Soc. 1993, 115, 7944. (g) Wender, P. A.; Zercher, C. K.; Beckham, S.; Haubold, E.-M. J. Org. Chem. 1993, 58, 5867.
10. (a) Semmelhack, M. F.; Gallagher, J.; Cohen, D. Tetrahedron Lett. 1990, 31, 1521.
11. (b) Langley, D. R.; Doyle, T. W.; Beveridge, D. L. J. Am. Chem. Soc. 1991, 113, 4395.
12. For references on the synthesis of the anthraquinone subunit, see: (a) Chikashita, H.; Porco, J. A., Jr.; Stout, T. J.; Clardy, J.; Schreiber, S. L. J. Org. Chem. 1991, 56, 1692. (b) Nicolaou, K. C.; Gross, J. L.; Kerr, M. A.; Lemus, R. H.; Ikeda, K.; Ohe, K. Angew. Chem., Int. Ed. Engl. 1994, 33, 781. (c) Okita, T.; Isobe, M. Tetrahedron 1994, 38, 11143.
13. For references on the synthesis of the anthraquinone subunit, see: (a) Chikashita, H.; Porco, J. A., Jr.; Stout, T. J.; Clardy, J.; Schreiber, S. L. J. Org. Chem. 1991, 56, 1692. (b) Nicolaou, K. C.; Gross, J. L.; Kerr, M. A.; Lemus, R. H.; Ikeda, K.; Ohe, K. Angew. Chem., Int. Ed. Engl. 1994, 33, 781. (c) Okita, T.; Isobe, M. Tetrahedron 1994, 38, 11143.
14. For references on the synthesis of the anthraquinone subunit, see: (a) Chikashita, H.; Porco, J. A., Jr.; Stout, T. J.; Clardy, J.; Schreiber, S. L. J. Org. Chem. 1991, 56, 1692. (b) Nicolaou, K. C.; Gross, J. L.; Kerr, M. A.; Lemus, R. H.; Ikeda, K.; Ohe, K. Angew. Chem., Int. Ed. Engl. 1994, 33, 781. (c) Okita, T.; Isobe, M. Tetrahedron 1994, 38, 11143.
15. Pérez, D.; Guitián, E.; Castedo, L. J. Org. Chem. 1992, 57, 5911.
16. Grewe, R.; Mondon, A. Chem. Ber. 1948, 279.
17. Schmidt, R. R.; Betz, R. Synthesis 1982, 748.
18. (a) Logullo, F. M.; Seitz, A. H.; Friedman, L. Org. Synth. 1968, 48, 12.
19. (b) For a general procedure for intermolecular benzyne cycloadditions, see: Atanes, N.; Castedo, L.; Guitián, E.; Saá, C.; Saá, J. M.; Suau, R. J. Org. Chem. 1991, 56, 2984.
20. Cheng, C. C.; Zee-Cheng, R. K. Y. Heterocycles 1981, 15, 1275.