Enantioselective synthesis of a PKC inhibitor via catalytic C-H bond activation

Organic Letters

Volumn 8, Issue 8, 2006, Pages 1745-1747

  Wilson, Rebecca M ^a   Thalji, Reema K ^a   Bergman, Robert G ^a   Ellman, Jonathan A ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

INDOLE DERIVATIVE; PROTEIN KINASE C;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; DRUG ANTAGONISM; STEREOISOMERISM; STRUCTURE ACTIVITY RELATION; SYNTHESIS;

CATALYSIS; INDOLES; MOLECULAR STRUCTURE; PROTEIN KINASE C; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 33646466149     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol060485h     Document Type: Article

References (23)

1. 2C receptor ligands. Int. Pat. Appl. WO 02/051844 A1, July 4, 2002.
2. (b) Wang, Z.; Dufresne, C.; Guay, D.; Leblanc, Y. Dihydropyrrolo[1,2-a] indole and Tetrahydropyrido[1,2-a]indole Derivatives as Prostaglandin D2 Receptor Antagonists. Int. Pat. Appl. WO 02/094830 A2, Nov 28, 2002.
3. For a review on the mitomycinoids, see: (c) Danishefsky, S. J.; Schkeryantz, J. M. Synlett 1995, 475-490.
4. 2C Agonists. US Patent 6,433,175 B1, Aug 13, 2002.
5. Inaba, T.; Tanaka, M.; Sakoda, K. Disubstituted Maleimide Compounds and Medicinal Utilization Thereof. Eur. Pat. Appl. 1,120,414 A1, Aug 1, 2001.
6. (a) Thalji, R. K.; Ahrendt, K. A.; Bergman, R. G.; Ellman, J. A. J. Am. Chem. Soc. 2001, 123, 9692-9693.
7. (b) Thalji, R. K.; Ellman, J. A.; Bergman, R. G. J. Am. Chem. Soc. 2004, 126, 7192-7193.
8. For examples of the application of C-H bond activation in target-oriented synthesis, see: (a) Harris, P. W. R.; Woodgate, P. D. J. Organomet. Chem. 1997, 530, 211-223.
9. (b) Johnson, J. A.; Sames, D. J. Am. Chem. Soc. 2000, 122, 6321-6322.
10. (c) Dangel, B. D.; Godula, K.; Youn, S. W.; Sezen, B.; Sames, D. J. Am. Chem. Soc. 2002, 124, 11856-11857.
11. (d) Wehn, P. M.; Du Bois, J. J. Am. Chem. Soc. 2002, 124, 12950-12951.
12. (e) Ahrendt, K. A.; Bergman, R. G.; Ellman, J. A. Org. Lett. 2003, 5, 1301-1303.
13. (f) Pastine, S. J.; Sames, D. Org. Lett. 2003, 5, 4053-4055.
14. (g) O'Malley, S. J.; Tan, K. L.; Watzke, A.; Bergman, R. G.; Ellman, J. A. J. Am. Chem. Soc. 2005, 127, 13496-13497.
15. For examples of the application of rhodium-carbenoid insertions into C-H bonds in target-oriented synthesis, see: (a) Taber, D. F.; Song, Y. J. Org. Chem. 1997, 62, 6603-6607.
16. (b) Davies, H. M. L.; Stafford, D. G.; Hansen, T. Org. Lett. 1999, 1, 233-236.
17. (c) Davies, H. M. L.; Gregg, T. M. Tetrahedron Lett. 2002, 43, 4951-4953 and references therein.
18. (a) Kakiuchi, F.; Sekine, S.; Tanaka, Y.; Kamatani, A.; Sonoda, M.; Chatani, N.; Murai, S. Bull. Chem. Soc. Jpn. 1995, 68, 62-83.
19. (b) Jun, C. H.; Moon, C. W.; Hong, J. B.; Lim, S. G.; Chung, K. Y.; Kim, Y. H. Chem. Eur. J. 2002, 8, 485-492.
20. Lenges, C. P.; Brookhart, M. J. Am. Chem. Soc. 1999, 121, 6616-6623.
21. Meyer, M. D.; Kruse, L. I. J. Org. Chem. 1984, 49, 3195-3199.
22. 3 gave 0% conversion under identical conditions.
23. Shen, L.; Prouty, C.; Conway, B. R.; Westover, L.; Xu, J. Z.; Look, R. A.; Chen, X.; Beavers, M. P.; Roberts, J.; Murray, W. V.; Demarest, K. T.; Kuo, G. H. Bioorg. Med. Chem. 2004, 12, 1239-1255.