A concise synthesis of butylcycloheptylprodigiosin

Organic Letters

Volumn 9, Issue 10, 2007, Pages 1879-1881

  Reeves, Jonathan T ^a  

^a BOEHRINGER INGELHEIM PHARMACEUTICALS INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BUTYLCYCLOHEPTYLPRODIGIOSIN; DRUG DERIVATIVE; FORMIC ACID; FORMIC ACID DERIVATIVE; KETONE; PRODIGIOSIN; UNCLASSIFIED DRUG;

CHEMICAL STRUCTURE; CHEMISTRY; CONFERENCE PAPER; HYDROLYSIS; HYDROXYLATION; SYNTHESIS;

FORMIC ACIDS; HYDROLYSIS; HYDROXYLATION; KETONES; MOLECULAR STRUCTURE; PRODIGIOSIN;

EID: 34249330916     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol070341i     Document Type: Conference Paper

References (31)

1. For a review on the history, biology, and synthetic chemistry of the prodigiosin alkaloids, see: Fürstner, A. Angew. Chem., Int. Ed. 2003, 42, 3582-3603.
2. (a) Pérez-Tomás, R.; Montaner, B.; Llagostera, E.; Soto-Cerrato, V. Biochem. Pharm. 2003, 66, 1447-1452.
3. (b) Manderville, R. A. Curr. Med. Chem. Anti-Cancer Agents 2001, 1, 195-218.
4. (a) Dairi, K.; Tripathy, S.; Attardo, G.; Lavallee, J.-F. Tetrahedron Lett. 2006, 47, 2605-2606.
5. (b) Stepkowski, S. M.; Erwin-Cohen, R. A.; Behbod, F.; Wang, M. E.; Qu, X.; Tejpal, N.; Nagy, Z. S.; Kahan, B. D.; Kirken, R. A. Blood 2002, 99, 680-689.
6. (c) Stepkowski, S. M.; Nagy, Z. S.; Wang, M.-E.; Behbod, F.; Erwin-Cohen, R.; Kahan, B. D.; Kirken, R. A. Transplant. Proc. 2001, 33, 3272-3273.
7. (d) D'Alessio, R.; Bargiotti, A.; Carlini, O.; Colotta, F.; Ferrari, M.; Gnocchi, P.; Isetta, A.; Mongelli, N.; Motta, P.; Rossi, A.; Rossi, M.; Tibolla, M.; Vanotti, E. J. Med. Chem. 2000, 43, 2557-2565.
8. (e) Mortellaro, A.; Songia, S.; Gnocchi, P.; Ferrari, M.; Fornasiero, C.; D'Alessio, R.; Isetta, A.; Colotta, F.; Golay, J. J. Immunol. 1999, 162, 7102-7109.
9. (f) Magae, J.; Miller, M. W.; Nagai, K.; Shearer, G. M. J. Antibiot. 1996, 49, 86-90.
10. (g) Nakamura, A.; Magae, J.; Tsuji, R. F.; Yamasaki, M.; Nagai, K. Transplantation 1989, 47, 1013-1016.
11. (a) Gerber, N. N. J. Antibiot. 1975, 28, 194-199.
12. (b) Gerber, N. N.; Stahly, D. P. Appl. Microbiol. 1975, 30, 807-810.
13. Tsao, S. W.; Rudd, B. A. M.; He, X. G.; Chang, C. J.; Floss, H. G. J. Antibiot. 1985, 38, 128-131.
14. Laatsch, H.; Kellner, M.; Weyland, H. J. Antibiot. 1991, 44, 187-191.
15. (a) Fürstner, A.; Radkowski, K.; Peters, H. Angew. Chem., Int. Ed. 2005, 44, 2777-2781.
16. (b) Fürstner, A.; Radkowski, K.; Peters, H.; Seidel, G.; Wirtz, C.; Mynott, R.; Lehmann, C. W. Chem. Eur. J. 2007, 13, 1929-1945.
17. Reeves, J. T.; Song, J. J.; Tan, Z.; Lee, H.; Yee, N. K.; Senanayake, C. H. Org. Lett. 2007, 9, XX-XX (ol070340q).
18. D'Alessio, R.; Rossi, A. Synlett 1996, 513-514.
19. (a) Fürstner, A.; Grabowski, J.; Lehmann, C. W. J. Org. Chem. 1999, 64, 8275-8280.
20. (b) Fürstner, A.; Krause, H. J. Org. Chem. 1999, 64, 8281-8286.
21. (c) Fürstner, A.; Grabowski, J.; Lehmann, C. W.; Kataoka, T.; Nagai, K. ChemBioChem 2001, 2, 60-68.
22. (d) Fürstner, A.; Reinecke, K.; Prinz, H.; Waldmann, H. ChemBioChem 2004, 5, 1575-1579.
23. Nicolaou, K. C.; Montagnon, T.; Baran, P. S.; Zhong, Y. L. J. Am. Chem. Soc. 2002, 124, 2245-2258.
24. (a) Stork, G.; d'Angelo, J. J. Am. Chem. Soc. 1974, 96, 7114-7116.
25. (b) Heng, K. K.; Smith, R. A. J. Tetrahedron 1979, 35, 425-435.
26. (c) Taylor, R. J. K. Synthesis 1985, 364-392.
27. (d) Suzuki, M.; Kawagishi, T.; Yanagisawa, A.; Suzuki, T.; Okamura, N.; Noyori, R. Bull. Chem. Soc. Jpn. 1988, 61, 1299-1312.
28. (e) Nicolaou, K. C.; Tang, W.; Dagneau, P.; Faraoni, R. Angew. Chem., Int. Ed. 2005, 44, 3874-3879.
29. Kitamura, M.; Nakano, K.; Miki, T.; Okada, M.; Noyori, R. J. Am. Chem. Soc. 2001, 123, 8939-8950.
30. 1H NMR signals for the two oxazole hydrogens and the vinyl hydrogen are significantly further downfidd for E-8 than Z-8 (see the Supporting Information for complete spectral data), which also suggests lesser conjugation of the oxazole with the ketone carbonyl in Z-8.
31. Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457-2483.