Total synthesis of the β-caten in inhibitor, (-)-agelastatin A: A second-generation approach based on radical aminobromination

Organic Letters

Volumn 11, Issue 15, 2009, Pages 3402-3405

  Yoshimitsu, Takehiko ^a   Ino, Tatsunori ^a   Futamura, Naoyuki ^a   Kamon, Takuma ^a   Tanaka, Tetsuaki ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

AGELASTATIN A; ALKALOID; ANTINEOPLASTIC AGENT; BETA CATENIN; IRON DERIVATIVE; OXAZOLIDINONE DERIVATIVE;

ARTICLE; CHEMISTRY; DRUG ANTAGONISM; SYNTHESIS;

ALKALOIDS; ANTINEOPLASTIC AGENTS; BETA CATENIN; IRON COMPOUNDS; OXAZOLIDINONES;

EID: 68149141337     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol9012684     Document Type: Article

References (31)

1. (a) D'Ambrosio, M.; Guerriero, A.; Debitus, C.; Ribes, O.; Pusset, J.; Leroy, S.; Pietra, F. J. Chem. Soc, Chem. Commun. 1993, 1305.
2. (b) Guerriero, A.; D'Ambrosio, M.; Chiasera, G.; Pietra, F. Helv. Chim. Acta 1994, 77, 1895.
3. (c) D'Ambrosio, M.; Guerriero, A.; Ripamonti, M.; Debitus, C.; Waikedre, J.; Pietra, F. Helv. Chim. Acta 1996, 79, 727.
4. (d) Hong, T. M.; Jimenez, D. R.; Molinski, T. F. J. Nat. Prod. 1998, 67, 158.
5. (e) Pettit, G. R.; Ducki, S.; Herald, D. L.; Doubek, D. L.; Schmidt, J. M.; Chapuis, J.-C. Oncol. Res. 2005, 15, 11.
6. Total syntheses of agelastatin A: (a) Anderson, G. T.; Chase, C. E.; Koh, Y.-H.; Stien, D.; Weinreb, S. M.; Shang, M. J. Org. Chem. 1998, 63, 7594.
7. (b) Stien, D.; Anderson, G. T.; Chase, C. E.; Koh, Y.-H.; Weinreb, S. M. J. Am. Chem. Soc. 1999, 121, 9574.
8. (c) Feldman, K. S.; Saunders, J. C. J. Am. Chem. Soc. 2002, 124, 9060.
9. (d) Feldman, K. S.; Saunders, J. C.; Wrobleski, M. L. J. Org. Chem. 2002, 67, 7096.
10. (e) Hale, K. J.; Domostoj, M. M.; Tocher, D. A.; Irving, E.; Scheinmann, F. Org. Lett. 2003, 5, 2927.
11. (f) Domostoj, M. M.; Irving, E.; Scheinmann, F.; Hale, K. J. Org. Lett. 2004, 6, 2615.
12. (g) Davis, F. A.; Deng, J. Org. Lett. 2005, 7, 621.
13. (h) Trost, B. M.; Dong, G. J. Am Chem. Soc. 2006, 128, 6054.
14. (i) Ichikawa, Y.; Yamaoka, T.; Nakano, K.; Kotsuki, H. Org. Lett. 2007, 9, 2989.
15. (j) Dickson, D. P.; Wardrop, D. J. Org. Lett. 2009, 11, 1341.
16. (k) When, P. M.; Du Bois, J. Angew. Chem., Int. Ed. 2009, 48, 3802.
17. Hama, N.; Matsuda, T.; Sato, T.; Chida, N.; Org. Lett. 2009, 11, 2687.
18. (m) Davis, F. A.; Zhang, J.; Zhang, Y.; Qiu, H. Synth. Commun. 2009, 39, 1914.
19. (a) Mason, C. K.; McFarlane, S.; Johnston, P. G.; Crowe, P.; Erwin, P. J.; Domostoj, M. M.; Campbell, F. C.; Manaviazar, S.; Hale, K. J.; ElTanani, M. Mol. Cancer Ther. 2008, 7, 548.
20. (b) Hale, K. J.; Domostoj, M. M.; El-Tanani, M.; Campbell, F. C.; Mason, C. K. In Strategies and Tactics in Organic Synthesis; Harmata, M., Ed.; Academic Press: London, UK, 2005; p 352.
21. Yoshimistu, T.; Ino, T.; Tanaka, T. Org. Lett. 2008, 70, 5457.
22. Intermolecular aziridination approach to agelastatin core: Baron, E.; O'Brien, P.; Towers, T. D. Tetrahedron Lett. 2002, 43, 723.
23. (a) Bach, T.; Schlummer, B.; Harms, K. Chem. Commun. 2000, 287.
24. (b) Bach, T.; Schlummer, B.; Harms, K. Synlett 2000, 1330.
25. (c) Bach, T.; Schlummer, B.; Harms, K. Chem.-Eur. J. 2001, 7, 2581.
26. (d) Churchill, D. G.; Rojas, C. M. Tetrahedron Lett. 2002, 43, 7225.
27. (e) Bacci, J. P.; Greenman, K. L.; Van Vranken, D. L. J. Org. Chem. 2003, 68, 4955.
28. One can reasonably assume that heating compound 2 would lead to aziridine which, by ring-opening with the carbamoyl group at the 2-position of the pyrrole ring, would provide desired lactam 4. However, such attempts only gave a complex mixture without any detectable lactam 4.
29. 2 has been shown to form a stable terahydrate complex with water (Inorg. Chim. Acta, 1992, 192, 173). Because of its clarity, however, the mechanism shown in Schemes 1 and 3 omitted the solvating molecules.
30. 4NBr (1.5 equiv) gave only 35% of 3a. The origin of the retardation under these conditions is currently unclear.
31. 4NBr (Inorg. Synth. 1967, 9, 139). The present conditions may also produce such bis(tetraalkylammonium) tetrabromoferrate(II) complex in the reaction mixture. Nevertheless, our successful aminobromination reactions indicate that the iron(II) complex serves as an efficient radical mediator to deliver aminobromides.