Synthetic studies on the bicyclo[73.1]tridecenediyne system in an antitumor antibiotic, Dynemicin A

Synlett

Volumn 1991, Issue 6, 1991, Pages 393-395

  Nishikawa, Toshio ^a   Isobe, Minoru ^a   Goto, Toshio ^a  

^a NAGOYA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84989539663     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-1991-20738     Document Type: Article

References (29)

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2. Konishi, M.; Ohkuma, H.; Tsuno, T.; Oki, T.; VanDuyne, G. D.; Clardy, J. /. Am. Chem. Soc. 1990,112,3715.
3. deoxy-Dynemicin A: Shiomi, K.; Iinuma, H.; Naganawa, H.; Hamada, M.; Hattori, S.; Nakamara, H.; Takeuchi, T.; Iitaka, Y. /. Antibiot. 1990,43, 1000.
4. Golik, J.; Claidy, J.; Dubay, G.; Groenewold, G.; Kawaguchi, H.; Konishi, M; Kirshnan, B.; Ohkuma, H.; Saitoh, K.; Doyle, T. W. /. Am. Chem. Soc. 1987,109,3461.
5. Golik, J., G.; Groenewold, G.; Kawaguchi, H; Konishi, M.; Kirshnan, B.; Ohkuma, H.; Saitoh, K.; Doyle, T. ibid. 1987,109,3462.
6. Lee, M. D.; Dunne, T. S.; Siegel, M. M.; Chang, C. C; Morton, G. O; Borders, D. B. J. Am. Chem. Soc. 1987,109, 3464.
7. Lee, M. D.; Dunne. T. S.; Chang, C. C; EUestad, G. A.; Siegel, M. M.; Morton, G. O; McGahren, W. J.; Borders, D. B. ibid. 1987,109,3466.
8. Semmelhack, M. F.; Gallagher, J.; Cohen, D. Tetrahedron Lett. 1990,31,1521.
9. Sugiura, Y.; Shiraki, T.; Konishi, M.; Oki, T. Proc. Natl. Acad. Soc. USA 1990,87,3831.
10. Snyder, J. P.; Tipsword, G. E. J. Am. Chem. Soc. 1990,112,4040.
11. Isobe, M.; Nishikawa, T.; Goto, T. Int. Chem. Congr. Pacific Basin Soc.(Honolulu) 1989, Organic Chemistry, Abstract 183.
12. lsobe, M.; Nishikawa, T.; Herunsalee, A.; Tsukiyama, T.; Hirose, Y.; Shimokawa, K.; Goto, T. Pure &Appl. Chem. 1990, 62,2007.
13. Isobe, M.; Hirose, Y.; Shimokawa, K.; Nishikawa, T.; Goto, T. Tetrahedron Lett. 1990,31,5499.
14. Nishikawa, T.; Isobe, M.; Goto. T. Synlett 1991,99.
15. Another synthetic studies
16. Porco, Jr., J. A.; Stout, F. J.; Claidy, J.; Schreiber, S. L. /. Am. Chem. Soc. 1990,112,7410.
17. Nicolaou, K. C; Hwang, C. K.; Smith, A. L.; Wendeborn, S. V. ibid. 1990,112,7416.
18. Wender, P. A.; Zercher, C. K. /. Am. Chem. Soc. 1991,113,2311.
19. Preparation of 7 (R=Br): Furukawa, T.; Horiguchi.; Y.; Kuwajima, 1.32nd Symposium on the Chemistry of Natural Products. Symposium Papers 41 l(Chiba, 1990).
20. Similar route to the corresponding aldehyde of 9 was reported: Quesada, M. L.; Schlessinger, R. H. Synthetic Commun. 1976,6, 555.
21. Kende, A. S.; Smith, C. A. Tetrahedron Lett. 1988,29,4217.
22. Sonogashira, K.; Tohda, Y.; Hagihara, N. Tetrahedron Lett. 1975,4467.
23. Chemical proof was demonstrated at the stage of macro-ring cyclization into 17.
24. Parikh, J. R.; Doering, W. V. E. /. Am. Chem. Soc. 1967,89, 5505.
25. 16: lH-NMR(200MHz, CDC13) 80.27(9H, s), 1.51-1.85(5H, m), 2.47-2.59(lH, m), 3.32(1H, d, J= 2Hz), 3.54(1H, s), 5.86(lH,dd, J= 11,2Hz), 5.93(1H, d, J= 11Hz), 8.81(1H, s). 1JC-NMR (125MHz, CDCb) 8 2.02,17.99,18.82,34.08,61.95,65.24, 70.25,80.43,84.81,85.40,96.36,120.09,120.13,197.35. ]
26. Imamoto, T.; Sugiura, Y.; Takiyama, N. Tetrahedron Lett. 1984,25,4233.
27. Recent application to synthesis of NCS-chr. analogue: Myers, A. G.; Harrington, P. M.; Kuo, E.Y. J. Am. Chem. Soc. 1991,113,694.
28. 17:1H-NMR(200MHz, CDCb) 8 0.21(9H, s), l.61-1.96(5H, m), 2.08(1H, d, J= 4Hz, exchangeable with D2O), 2.17-2.32(1H, m), 3.21(1H, s), 4.33(1H, d, J= 4Hz), 5.93(1H, d, J= 10Hz), 5.99(1H, d, J= 10Hz). i3C-NMR(125MHz, CDCb) 81.78,19.56, 20.24,32.67,64.91,67.92,70.28,72.20,86.80,92.11,98.30, 100.12,122.55,122.83.
29. 19 (R=Ac): iH-NMR(270MHz, CDCb) 8 1.90-2.50(4H, in), 2.14(3H, s), 2.15(3H, s), 5.40(1H, s), 5.75(1H, s), 5.89(1H, d, J= 10Hz), 5.95(1H, d, J= 10Hz), 6.08(1H, t, J= 3Hz).