Asymmetric total synthesis of (-)-spirofungin A and (+)-spirofungin B

Organic Letters

Volumn 7, Issue 25, 2005, Pages 5573-5576

  Shimizu, Takeshi ^a   Satoh, Tomoharu ^a   Murakoshi, Katsunori ^a   Sodeoka, Mikiko ^a  

^a INST OF PHYS AND CHEMICAL RESEARCH   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIFUNGAL AGENT; PYRAN DERIVATIVE; SPIRO COMPOUND; SPIROFUNGIN A; SPIROFUNGIN B;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; CYCLIZATION; STEREOISOMERISM; STREPTOMYCES; SYNTHESIS;

ANTIBIOTICS, ANTIFUNGAL; CATALYSIS; CYCLIZATION; MOLECULAR STRUCTURE; PYRANS; SPIRO COMPOUNDS; STEREOISOMERISM; STREPTOMYCES;

EID: 29444447467     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol052039k     Document Type: Article

References (30)

1. Holtzel, A.; Kempter, C.; Metzger, J. W.; Jung, G.; Groth, I.; Fritz, T.; Fiedler, H.-P. J. Antibiot. 1998, 51, 699.
2. (a) Takahashi, H.; Osada, H.; Koshino, H.; Kudo, T.; Amano, S.; Shimizu, S.; Yoshihama, M.; Isono, K. J. Antibiot. 1992, 45, 1409.
3. (b) Takahashi, H.; Osada, H.; Koshino, H.; Sasaki, M.; Onose, R.; Nakakoshi, M.; Yoshihama, M.; Isono, K. J. Antibiot. 1992, 45, 1414.
4. (c) Koshino, H.; Takahashi, H.; Osada, H.; Isono, K. J. Antibiot. 1992, 45, 1420.
5. (d) Ubukata, M.; Koshino, H.; Osada, H.; Isono, K. J. Chem. Soc., Chem. Commun. 1994, 1877.
6. The absolute configurations depicted for 1 and 2 were proposed by analogy with 3 and remained unconfirmed until our total synthesis.
7. Zanatta, S. D.; White, J. M.; Rizzacasa, M. A. Org. Lett. 2004, 6, 1041.
8. Shimizu, T.; Masuda, T.; Hiramoto, K.; Nakata, T. Org. Lett. 2000, 2, 2153.
9. A second total synthesis: El Sous, M.; Ganame, D.; Tregloan, P. A.; Rizzacasa, M. A. Org. Lett. 2004, 6, 3001.
10. Shimizu, T.; Usui, T.; Machida, K.; Furuya, K.; Osada, H.; Nakata, T. Bioorg. Med. Chem. Lett. 2002, 12, 3363.
11. Synthetic studies on the spiroketal parts of spirofungin A and B: (a) Shimizu, Y.; Kiyota, H.; Oritani, T. Tetrahedron Lett. 2000, 41, 3141.
12. (b) Shimizu, T.; Kusaka, J.; Ishiyama, H.; Nakata, T. Tetrahedron Lett. 2003, 44, 4965.
13. (c) Dias, L. C.; de Oliveira, L. G. Org. Lett. 2004, 6, 2587.
14. (d) La Cruz, T. E.; Rychnovsky, S. D. Org. Lett. 2005, 7, 1873.
15. (a) Miyaura, N.; Yamada, Y.; Suzuki, A. Tetrahedron Lett. 1979, 20, 3437.
16. (b) Miyaura, N.; Suginome, H.; Suzuki, A. Tetrahedron Lett. 1981, 22, 127.
17. (c) Suzuki, A. Pure Appl. Chem. 1985, 57, 1749.
18. (d) Takagi, J.; Takahashi, K.; Isiyama, T.; Miyaura, N. J. Am. Chem. Soc. 2002, 124, 8001.
19. For the synthesis of 8, 9, and 10, see the Supporting Information.
20. Oshima, M.; Yamazaki, H.; Shimizu, I.; Nisar, M.; Tsuji, J. J. Am. Chem. Soc. 1989, 111, 6280.
21. Yamaguchi, M.; Hirao, I. Tetrahedron Lett. 1983, 24, 391.
22. 2OMe) corresponding to 14, 15, and 16 revealed an energy difference of only 0.08 kcal/mol, which means a 46:54 ratio of 17a/18a.
23. (a) Hart, D. W.; Glackburn, T. F.; Schwarz, J. J. Am. Chem. Soc. 1975, 97, 679.
24. (b) Panek, J. S.; Hu, T. J. Org. Chem. 1997, 62, 4912.
25. (c) Drouet, K. E.; Theodorakis, E. A. J. Am. Chem. Soc. 1999, 121, 456.
26. (d) Thompson, C. F.; Jamison, T. F.; Jacobsen, E. N. J. Am. Chem. Soc. 2001, 123, 9974.
27. (a) Takai, K.; Nitta, K.; Utimoto, K. J. Am. Chem. Soc. 1986, 108, 7408.
28. (b) Pontikis, R.; Musci, A.; Le Merrer, Y. Bull. Soc. Chim. Fr. Part 2 1991, 968.
29. Corey, E. J.; Katzenellenbogen, J. A.; Roman, S. A.; Gilman, N. W. Tetrahedron Lett. 1971, 21, 1821.
30. 2Me) suggested a large energy difference (4.19 kcal/mol) in favor of 17b.