Asymmetric syntheses of (-)-mitorubrin and related azaphilone natural products

Organic Letters

Volumn 8, Issue 22, 2006, Pages 5169-5171

  Zhu, Jianglong ^a   Porco Jr , John A ^a  

^a Boston University   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AZAPHILONE; BENZOIC ACID DERIVATIVE; BENZOPYRAN DERIVATIVE; BIOLOGICAL PRODUCT; MITORUBRIN; PIGMENT;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

BENZOIC ACIDS; BENZOPYRANS; BIOLOGICAL PRODUCTS; MOLECULAR STRUCTURE; PIGMENTS, BIOLOGICAL; STEREOISOMERISM;

EID: 33750926655     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol062233m     Document Type: Article

References (29)

1. (a) Buchi, G.; White, J. D.; Wogan, G. N. J. Am. Chem. Soc. 1965, 87, 3484.
2. (b) Locci, R.; Merlini, L.; Nasini, G.; Locci, J. R. Giorn. Microbiol. 1967, 15, 93.
3. (c) Suzuki, S.; Hosoe, T.; Nozawa, K.; Yaguchi, T.; Udagawa, S.; Kawai, K. J. Nat. Prod. 1999, 62, 1328.
4. (a) Natsume, M.; Takahashi, Y.; Marumo, S. Agric. Biol. Chem. 1985, 49, 2517.
5. (b) Lesova, K.; Sturdikova, M.; Rosenberg, M. J. Basic Microbiol. 2000, 40, 365.
6. (a) Tabata, Y.; Ikegami, S.; Yaguchi, T.; Sasaki, T.; Hoshiko, S.; Sakuma, S.; Shin-Ya, K.; Seto, H. J. Antibiot. 1999, 52, 412.
7. (b) Oikawa, H.; Tokiwano, T. Nat. Prod. Rep. 2004, 21, 321.
8. (a) Steglich, W.; Klaar, M.; Furtner, W. Phytochemistry 1974, 13, 2874.
9. (b) Nozawa, K.; Saito, R.; Udagawa, S.; Nakajima, S.; Kawai, K. Phytochemistry 1995, 39, 719.
10. (c) Singh, S. B.; Kelly, R.; Guan, Z.; Polishook, J. D.; Dombrowski, A. W.; Collado, J.; Gonzalez, A.; Pelaez, F.; Register, E.; Kelly, T. M.; Bonfiglio, C.; Williamson, J. M. Nat. Prod. Res. 2005, 19, 739.
11. Nukina, M.; Marumo, S. Tetrahedron Lett. 1977, 18, 2603.
12. (a) Chong, R.; Gray, R. W.; King, R. R.; Whalley, W. B. J. Chem. Soc., Chem. Commun. 1970, 101.
13. (b) Whalley, W. B.; Chong, R.; Gray, R. W.; King, R. R. J. Chem. Soc. C 1971, 3571.
14. Marsini, M. A.; Gowin, K. M.; Pettus, T. R. R. Org. Lett. 2006, 8, 3481.
15. Zhu, J.; Germain, A. R.; Porco, J. A., Jr. Angew. Chem., Int. Ed. 2004, 43, 1239.
16. Zhu, J.; Grigoriadis, N. P.; Lee, J. P.; Porco, J. A., Jr. J. Am. Chem. Soc. 2005, 127, 9342.
17. (a) Hundertmark, T.; Littke, A. F.; Buchwald, S. L.; Fu, G. C. Org. Lett. 2000, 2, 1729.
18. (b) Netherton, M. R.; Fu, G. C. Org. Lett. 2001, 3, 4295.
19. See Supporting Information for complete experimental details.
20. 3N-mediated cycloisomerization, see: (a) Kel'in, A. V.; Sromek, A. W.; Gevorgyan, V. J. Am. Chem. Soc. 2001, 123, 2074.
21. (b) Kel'in, A. V.; Gevorgyan, V. J. Org. Chem. 2002, 67, 95.
22. (a) Roush, W. R.; Murphy, M. J. Org. Chem. 1992, 57, 6622.
23. (b) Hurd, R. N.; Shah, D. H. J. Org. Chem. 1973, 38, 607 (ref 9 therein).
24. Chhabra, B. R.; Hayano, K.; Ohtsuka, T.; Shirahama, H.; Matsumoto, T. Chem. Lett. 1981, 1703.
25. (a) Blackwell, H. E.; O'Leary, D. J.; Chatterjee, A. K.; Washenfelder, R. A.; Bussmann, D. A.; Grubbs, R. H. J. Am. Chem. Soc. 2000, 122, 58.
26. (b) Chatterjee, A. K.; Grubbs, R. H. Angew. Chem., Int. Ed. 2002, 41, 3172.
27. (c) Connon, S. J.; Blechert, S. Angew. Chem., Int. Ed. 2003, 42, 1900.
28. Garber, S. B.; Kingsbury, J. S.; Gray, B. L.; Hoveyda, A. H. J. Am. Chem. Soc. 2000, 122, 8168.
29. 2O, see: Moriwake, T.; Hamano, S.; Miki, D.; Saito, S.; Torii, S. Chem. Lett. 1986, 815.