Tandem intramolecular Michael-Aldol reaction as a tool for the construction of the C-ring of hexacyclinic acid

Organic Letters

Volumn 8, Issue 16, 2006, Pages 3485-3488

  Stelmakh, Andriy ^a   Stellfeld, Timo ^a,b   Kalesse, Markus ^a  

^a LEIBNIZ UNIVERSITY HANNOVER   (Germany)

^b BAYER PHARMA AG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

FUSED HETEROCYCLIC RINGS; HEXACYCLINIC ACID; MACROLIDE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; CONFORMATION; STREPTOMYCES; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

CRYSTALLOGRAPHY, X-RAY; HETEROCYCLIC COMPOUNDS WITH 4 OR MORE RINGS; MACROLIDES; MOLECULAR CONFORMATION; MOLECULAR STRUCTURE; STREPTOMYCES;

EID: 33747243871     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol061096q     Document Type: Article

References (25)

1. Höfs, R.; Walker, M.; Zeeck, A. Angew. Chem., Int. Ed. 2000, 39, 3258-3261.
2. Sato, B.; Muramatsu, H.; Miyauchi, M.; Hori, Y.; Takase, S.; Hino, M.; Hashimoto, S.; Terano, H. J. Antibiot. 2000, 53, 123-130.
3. Edler, M. C.; Buey, R. M.; Gussio, R.; Marcus, A. I.; Vanderwal, C. D.; Sorensen, E. J.; Diaz, J. F.; Giannakakou, P.; Hamel, E. Biochemistry 2005, 44, 11525-11538.
4. (a) Vosburg, D. A.; Vanderwal, C. D.; Sorensen, E. J. J. Am. Chem. Soc. 2002, 124, 4552-4553.
5. (b) Vanderwal, C. D.; Vosburg, D. A.; Weiler, S.; Sorensen, E. J. J. Am. Chem. Soc. 2003, 125, 5393-5407.
6. (c) Evans, D. A.; Starr, J. T. Angew. Chem., Int. Ed. 2002, 41, 1787-1790.
7. (d) Evans, D. A.; Starr, J. T. J. Am. Chem. Soc. 2003, 125, 13531-13540.
8. (a) Clarke, P. A.; Grist, M.; Ebden, M.; Wilson, C. Chem. Commun. 2003, 1560-1561.
9. (b) Clarke, P. A.; Grist, M.; Ebden, M. Tetrahedron Lett. 2004, 45, 927-929.
10. (c) Clarke, P. A.; Cridland, A. P. Org. Lett. 2005, 7, 4221-4224.
11. (d) Clarke, P. A.; Davie, R. L.; Peace, S. Tetrahedron 2005, 61, 2335-2351.
12. (e) James, P.; Felpin, F.-X.; Landais, Y.; Schenk, K. J. Org. Chem. 2005, 70, 7985-7995.
13. (f) Funel, J.; Prunet, J. J. Org. Chem. 2004, 69, 4555-4558.
14. (g) Methot, J. L.; Roush, W. R. Org. Lett. 2003, 5, 4223-4226.
15. Stellfeld, T.; Bhatt, U.; Kalesse, M. Org. Lett. 2004, 6, 3889-3892.
16. (a) Ihara, M.; Ohnishi, M.; Takano, M.; Makita, K.; Taniguchi, N.; Fukumoto, K. J. Am. Chem. Soc. 1992, 114, 4408-4410.
17. (b) Ihara, M.; Taniguchi, T.; Makita, K.; Takano, M.; Ohnishi, M.; Taniguchi, N.; Fukumoto, K.; Kabuto, C. J. Am. Chem. Soc. 1993, 115, 8107-8115.
18. (c) Ihara, M.; Taniguchi, T.; Tokunaga, Y.; Fukumoto, K. J. Org. Chem. 1994, 59, 8092-8100.
19. (d) Ihara, M.; Taniguchi, T.; Yamada, M.; Tokunaga, Y.; Fukumoto, K. Tetrahedron Lett. 1995, 36, 8071-8074.
20. (e) Takasu, K.; Ueno, M.; Ihara, M. Tetrahedron Lett. 2000, 41, 2145-2148.
21. Takakis, I. M.; Tsantali G. G. J. Org. Chem. 2003, 68, 6455-6458.
22. (a) Horiguchi, Y.; Matsuzawa, S.; Nakamura, E.; Kuwajima, I. Tetrahedron Lett. 1986, 27, 4025-4028.
23. (b) Nakamura, E.; Matsuzawa, S.; Horiguchi, Y.; Kuwajima, I. Tetrahedron Lett. 1986, 27, 4029-4032.
24. Büchi, G.; Wuest, H. J. Org. Chem. 1969, 34, 1122-1123.
25. See the Supporting Information for details on the HPLC separation of 11.