Total synthesis of (+)-yatakemycin

Journal of the American Chemical Society

Volumn 128, Issue 22, 2006, Pages 7136-7137

  Okano, Kentaro ^a   Tokuyama, Hidetoshi ^a,b   Fukuyama, Tohru ^a  

^a UNIVERSITY OF TOKYO   (Japan)

^b TOHOKU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

2,6 DIBROMOPHENYLLITHIUM; ANTINEOPLASTIC ANTIBIOTIC; BICARBONATE; BROMINE; COPPER DERIVATIVE; CYCLOPROPANE; EPICHLOROHYDRIN; LITHIUM DERIVATIVE; UNCLASSIFIED DRUG; YATAKEMYCIN;

ANTINEOPLASTIC ACTIVITY; ARTICLE; BROMINATION; DNA ALKYLATION; DRUG STRUCTURE; DRUG SYNTHESIS; STREPTOMYCES;

ANTINEOPLASTIC AGENTS; INDOLES; MOLECULAR STRUCTURE; PYRROLES; STEREOISOMERISM;

EID: 33744928097     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0619455     Document Type: Article

References (30)

1. Igarashi, Y.; Futamata, K.; Fujita, T.; Sekine, A.; Senda, H.; Naoki, H.: Furumai, T. J. Antibiot. 2003, 56, 107.
2. (a) Boger, D. L.; Machiya, K. J. Am. Chem. Soc. 1992, 114, 10056.
3. (b) Fukuda, Y.; Terashima, S. Tetrahedron Lett. 1997, 38, 7207.
4. (c) Muratake, H.; Tonegawa, M.; Natsume, M. Chem. Pharm. Bull. 1998, 46, 400 and references therein.
5. (a) Fukuda, Y.; Itoh, Y.; Nakatani, K.; Terashima, S. Tetrahedron 1994, 50, 2793.
6. (b) Boger, D. L.; McKie, J. A.; Nishi, T.; Ogiku, T. J. Am. Chem. Soc. 1996, 118, 2301.
7. (a) Kelly, R. C.; Gebhard, I.; Wicnienski, N.; Aristoff, P. A.; Johnson, P. D.; Martin, D. G. J. Am. Chem. Soc. 1987, 109, 6837.
8. (b) Boger, D. L.; Coleman, R. S. J. Am. Chem. Soc. 1988, 110, 1321.
9. (c) Bolton, R. E.; Moody, C. J.; Pass, M.; Rees, C. W.; Tojo, G. J. Chem. Soc., Perkin Trans, 1 1988, 2491.
10. For a review on CC-1065 and duocarmycins, see: (d) Boger, D. L.; Boyce, C. W.; Garbaccio, R. M.; Goldberg, J. A. Chem. Rev. 1997, 97, 787.
11. (a) Parrish, J. P.; Kastrinsky, D. B.; Wolkenberg, S. E.; Igarashi, Y.; Boger, D. L. J. Am. Chem. Soc. 2003, 125, 10971.
12. (b) Tichenor, M. S.; Kastrinsky, D. B.; Boger, D. L. J. Am. Chem. Soc. 2004, 126, 8396.
13. (a) Yamada, K.; Kubo, T.; Tokuyama, H.; Fukuyama, T. Synlett 2002, 231.
14. (b) Okano, K.; Tokuyama, H.; Fukuyama, T. Org. Lett. 2003, 5, 4987.
15. For a review, see: (c) Ley, S. V.; Thomas, A. W. Angew. Chem., Int. Ed. 2003, 42, 5400.
16. (d) Kwong, F. Y.; Buchwald, S. L. Org. Lett. 2003, 5, 793.
17. (e) Ma, D.; Cai, Q.; Zhang, H. Org. Lett. 2003, 5, 2453.
18. Yamada, K.; Kurokawa, T.; Tokuyama, H.; Fukuyama, T. J. Am. Chem. Soc. 2003, 125, 6630.
19. Hsin, L.-W.; Dersch, C. M.; Baumann, M. H.; Stafford, D.; Glowa, J. R.; Rothman, R. B.; Jacobson, A. E.; Rice, K. C. J. Med. Chem. 2002, 45, 1321.
20. Staudinger, H.; Meyer, J. Helv. Chim. Acta 1919, 2, 635.
21. Kan, T.; Fukuyama, T. Chem. Commun. 2004, 353.
22. For the details of catalytic amination, see Supporting Information.
23. Beletskaya, I. P.; Cheprakov, A. V. Chem. Rev. 2000, 100, 3009.
24. Kolar, A. J.; Olsen, R. K. Synthesis 1977, 457.
25. Venkov, A. P.; Lukanov, L. K. Synthesis 1989, 59.
26. Kelly, T. R.; Chandrakumar, N. S.; Saha, J. K. J. Org. Chem. 1989, 54, 980.
27. Maryanoff, B. E.; Reitz, A. B. Chem. Rev. 1989, 89, 863.
28. Rawal, V. H.; Cava, M. P. J. Am. Chem. Soc. 1986, 108, 2110.
29. For the preparation, see Supporting Information.
30. In the absence of pentamethylbenzene. 25 was obtained in low yield.