Synthesis of nonactin and the proposed structure of trilactone

Organic Letters

Volumn 8, Issue 13, 2006, Pages 2831-2834

  Wu, Yikang ^a   Sun, Ya Ping ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIINFECTIVE AGENT; LACTONE; MACROLIDE; NONACTIN; TRILACTONE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; CYCLIZATION; STREPTOMYCES GRISEUS; SYNTHESIS;

ANTI-BACTERIAL AGENTS; CYCLIZATION; LACTONES; MACROLIDES; MOLECULAR STRUCTURE; STREPTOMYCES GRISEUS;

EID: 33746121982     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0609661     Document Type: Article

References (37)

1. For reviews, see: (a) Keller-Schierlein, W.; Gerlach, H. Fortschr. Chem. Org. Naturst. 1968, 26, 161-189.
2. (b) Nawata, Y.; Ando, K.; Iitaka, Y. Met. Ions Biol. Syst. 1985, 19, 207-227.
3. (c) Zizka, Z. Folia Microbiol. 1998, 45, 7-14.
4. Nefelova, M. V.; Sverdlova, A. N. Antibiot. Med. Biotekhnol. 1985, 30, 261-264;
5. Chem. Abstr. 1985, 102, 201065.
6. (a) Oishi, H.; Sugawa, T.; Okutomi, T.; Suzuki, K.; Hayashi, T.; Sawada, M.; Ando, K. J. Antibiot. 1970, 23, 105-106.
7. (b) Shopotova, L. P.; Shenin, Y. D. Zh. Prikl. Khim. 1993, 66, 1334-1338;
8. Chem. Abstr. 1994, 120, 158329.
9. Borrel, M. N.; Pereira, E.; Fiallo, M.; Garnier-Suillerot, A. Eur. J. Biochem. 1994, 225, 125-133.
10. (a) Callewaert, D. M.; Radcliff, G.; Tanouchi, Y.; Shichi, H. Immunopharmacology 1988, 16, 25-32.
11. (b) Tanouchi, Y.; Shichi, H. Immunology 1988, 63, 471-475.
12. There are five total syntheses of nonactin in the literature: (a) Gerlach, H.; Oertle, K.; Thalmann, A.; Servi, S. Helv. Chim. Acta 1975, 58, 2036-2043.
13. (b) Schmidt, U.; Gombos, J.; Haslinger, E.; Zak, H. Chem. Ber. 1976, 109, 2628-2644.
14. (c) Bartlett, P. A.; Meadows, J. D.; Ottow, E. J. Am. Chem. Soc. 1984, 106, 5304-5311.
15. (d) Kim, B. H.; Lee, J. Y. Tetrahedron 1996, 52, 571-588.
16. (e) Fleming, I.; Ghosh, S. K. J. Chem. Soc., Perkin Trans. 1 1998, 2733-2747.
17. For a comprehensive review, see: (f) Fleming, I.; Ghosh, S. K. Stud. Nat. Prod. Chem. 1996, 18, 229-268.
18. For syntheses of nonactic acid published after 1996, see: (a) Bratt, K.; Garavelas, A.; Perlmutter, P.; Westman, G. J. Org. Chem. 1996, 61, 2109-2117.
19. (b) Kiyota, H.; Abe, M.; Ono, Y.; Oritani, T. Synlett 1997, 1093-1095.
20. (c) Takatori, K.; Tanaka, K.; Matsuoka, K.; Morishita, K.; Kajiwara, M. Synlett 1997, 159-160.
21. (d) Mandville, G.; Girard, C.; Bloch, R. Tetrahedron 1997, 53, 17079-17088.
22. (e) Meiners, U.; Cramer, E.; Frohlich, R.; Wibbeling, B.; Metz, P. Eur. J. Org. Chem. 1998, 2073-2078.
23. (f) Ahmar, M.; Duyck, C.; Fleming, I. J. Chem. Soc., Perkin Trans. 1 1998, 2721-2732.
24. (g) Lee, E.; Choi, S. J. Org. Lett. 1999, 1, 1127-1128.
25. (h) Wang, Y.; Metz, P. Tetrahedron: Asymmetry 2000, 11, 3995-3999.
26. (i) Fraser, B.; Perlmutter, P. J. Chem. Soc., Perkin Trans. 1 2002, 2896-2899.
27. (j) Jeong, J. W.; Woo, B. Y.; Ha, D. C.; No, Z. Synlett 2003, 393-395.
28. (k) Ireland, R. E.; Vevert, J. P. Can. J. Chem. 1981, 59, 572-583.
29. (l) Kim, B. H.; Lee, J. Y. Tetrahedron Lett. 1992, 33, 2557-2560. For other routes published by 1996, see ref 6f above.
30. Rezanka, R.; Spizek, J.; Prikrylova, V.; Prell, A.; Dembitskyb, V. M. Tetrahedron 2004, 60, 4781-4787.
31. Schaus, S. E.; Brandes, B. D.; Larrow, J. F.; Tokunaga, M.; Hansen, K. B.; Gould, A. E.; Furrow, M. E.; Jacobsen, E. N. J. Am. Chem. Soc. 2002, 124, 1307-1315 and references therein.
32. Evans, D. A.; Chapman, K. T.; Carreira, E. M. J. Am. Chem. Soc. 1988, 110, 3560-3578.
33. Crimmins, M. T.; King, B. W.; Tabet, E. A. J. Am. Chem. Soc. 1997, 119, 7883-7884.
34. Matsuda, F.; Kito, M.; Sakai, T.; Okada, N.; Miyashita, M.; Shirahama, H. Tetrahedron 1999, 55, 14369-14380.
35. Ager, D. J.; Allen, D. R.; Schaad, D. R. Synthesis 1996, 1283-1285.
36. Wu, Y.-K.; Huang, J.-H.; Shen, X.; Hu, Q.; Tang, C.-J.; Li, L. Org. Lett. 2002, 4, 2141-2144.
37. Nicolaou, K. C.; Bunnage, M. E.; McGarry, D. G.; Shi, S.; Somers, P. K.; Wallace, P. A.; Chu, X.-J.; Agrios, K. A.; Gunzner, J. L.; Yang, Z. Chem. Eur. J. 1999, 5, 599-617.