Total synthesis of kendomycin featuring intramolecular dötz benzannulation

Organic Letters

Volumn 12, Issue 8, 2010, Pages 1700-1703

  Tanaka, Kyosuke ^a   Watanabe, Masahito ^a   Ishibashi, Kodai ^a   Matsuyama, Hiroshi ^a   Saikawa, Yoko ^a   Nakata, Masaya ^a  

^a KEIO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CARBENE; CHROMIUM; DRUG DERIVATIVE; KENDOMYCIN; METHANE; RIFABUTIN;

ARTICLE; CHEMISTRY; SYNTHESIS; ULTRAVIOLET SPECTROPHOTOMETRY;

CHROMIUM; METHANE; RIFABUTIN; SPECTROPHOTOMETRY, ULTRAVIOLET;

EID: 77951156663     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol100229f     Document Type: Article

References (33)

1. For recent reviews on ansamycins, see
2. Funayama, S.; Cordell, G. A. In Studies in Natural Products Chemistry; Atta-ur-Rahman, Ed.; Elsevier Science: Amsterdam, 2000; Vol. 23, pp 51 - 106.
3. Floss, H. G.; Yu, T.-W. Chem. Rev. 2005, 105, 621-632
4. Bryskier, A. In Antimicrobial Agents; Bryskier, A., Ed; ASM Press: Washington, DC, 2005; pp 906 - 924.
5. Funahashi, Y.; Kawamura, N.; Ishimaru, T. Jpn. Kokai Tokkyo Koho 1996, 08231551
6. Chem. Abstr. 1996, 125, 326518.
7. Funahashi, Y.; Ishimaru, T.; Kawamura, N. Jpn. Kokai Tokkyo Koho 1996, 08231552
8. Chem. Abstr. 1997, 126, 6553.
9. Su, M. H.; Hosken, M. I.; Hotovec, B. J.; Johnston, T. L. U. S. Patent 5728727, 1998
10. Chem. Abstr. 1998, 128, 239489.
11. Bode, H. B.; Zeeck, A. J. Chem. Soc., Perkin Trans. 1 2000, 323-328
12. Yuan, Y.; Men, H.; Lee, C. J. Am. Chem. Soc. 2004, 126, 14720-14721
13. Smith, A. B., III.; Mesaros, E. F.; Meyer, E. A. J. Am. Chem. Soc. 2005, 127, 6948-6949
14. Smith, A. B., III.; Mesaros, E. F.; Meyer, E. A. J. Am. Chem. Soc. 2006, 128, 5292-5299
15. Lowe, J. T.; Panek, J. S. Org. Lett. 2008, 10, 3813-3816
16. Magauer, T.; Martin, H. J.; Mulzer, J. Angew. Chem., Int. Ed. 2009, 48, 6032-6036
17. Magauer, T.; Martin, H. J.; Mulzer, J. Chem. - Eur. J. 2010, 16, 507-519
18. Bahnck, K. B.; Rychnovsky, S. D. J. Am. Chem. Soc. 2008, 130, 13177-13181
19. Dötz, K. H. Angew. Chem., Int. Ed. Engl. 1975, 14, 644-645
20. Waters, M. L.; Wulff, W. D. In Organic Reactions; Overman, L. E., Ed.; Jon Wiley & Sons, Inc.: Hoboken, 2008; pp 121 - 623.
21. For a partial synthesis of kendomycin using the intermolecular Dötz reaction, see: White, J. D.; Smits, H. Org. Lett. 2005, 7, 235-238
22. Watanabe, M.; Tanaka, K.; Saikawa, Y.; Nakata, M. Tetrahedron Lett. 2007, 48, 203-206
23. Roush, W. R.; Palkowitz, A. D.; Ando, K. J. Am. Chem. Soc. 1990, 112, 6348-6359 for (+)- 6
24. Roush, W. R.; Coffey, D. S.; Madar, D. J. J. Am. Chem. Soc. 1997, 119, 11331-11332 for (-)- 6
25. Zeng, F.; Negishi, E. Org. Lett. 2002, 4, 703-706 and references therein
26. Hart, D. W.; Schwartz, J. J. Am. Chem. Soc. 1974, 96, 8115-8116
27. Yokokawa, F.; Asano, T.; Okino, T.; Gerwick, W. H.; Shioiri, T. Tetrahedron 2004, 60, 6859-6880
28. Chamberlin, S.; Wulff, W. D.; Bax, B. Tetrahedron 1993, 49, 5531-5547
29. Shih, T. L.; Wyvratt, M. J.; Mrozik, H. J. Org. Chem. 1987, 52, 2029-2033
30. Catechol monomethyl ether as an early-stage intermediate of kendomycin synthesis was prepared via the Dötz reaction, see ref 6.
31. For formation of o -quinone from monoprotected hydroquinone, see: Magdziak, D.; Rodriquez, A. A.; Van De Water, R. W.; Pettus, T. R. R. Org. Lett. 2002, 4, 285-288
32. For the synthesis of 26, triethylamine salt of 26, and 27, see the Supporting Information.
33. 2O was reported. See Janssen, C. O.; Lim, S.; Lo, E. P.; Wan, K. F.; Yu, V. C.; Lee, M. A.; Ng, S. B.; Everett, M. J.; Buss, A. D.; Lane, D. P.; Boyce, R. S. Bioorg. Med. Chem. Lett. 2008, 18, 5771-5773