General and efficient synthetic approach to novel tricyclic spiroketones

Tetrahedron

Volumn 65, Issue 27, 2009, Pages 5161-5167

  Chu, Guo Hua ^a   Le Bourdonnec, Bertrand ^a   Gu, Minghua ^a   Saeui, Christopher T ^a   Dolle, Roland E ^a  

^a ADOLOR CORPORATION   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

4 OXO 1 PIPERIDINECARBOXYLATE; CARBOXYLIC ACID DERIVATIVE; FUSED ALICYCLIC AROMATIC COMPOUND; INDANONE DERIVATIVE; KETONE DERIVATIVE; TETRALIN DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL PROCEDURES; CHEMICAL REACTION; CHEMICAL STRUCTURE; PRIORITY JOURNAL; SYNTHESIS;

EID: 66149138834     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2009.04.094     Document Type: Article

References (15)

1. Evans B.E., Rittle K.E., Bock M.G., Dipardo R.M., Freidinger R.M., Whitter W.L., Lundell G.F., Veber D.F., Anderson P.S., Chang R.S.L., Lotti V.J., Cerino D.J., Chen T.B., Kling P.J., Kunkel K.A., Springer J.P., and Hirschfield J. J. Med. Chem. 31 (1988) 2235-2246
2. Elliott J.M., Selnick H.G., Claremon D.A., Baldwin J.J., Buhrow S.A., Butcher J.W., Habecker C.N., King S.W., Lynch Jr. J.J., Phillips B.T., Ponticello G.S., Radzilowski E.M., Remy D.C., Stein R.B., White J.I., and Young M.B. J. Med. Chem. 35 (1992) 3973-3976
3. Tschaen D.V., Abramson L., Cai D., Desmond R., Dolling U.-H., Frey L., Karady S., Shi Y.-J., and Verhoeven T.R. J. Org. Chem. 60 (1995) 4324-4330
4. Nerenberg J.B., Erb J.M., Bergman J.M., O'Malley S., Chang R.S.L., Scott A.L., Broten T.P., and Bock M.G. Bioorg. Med. Chem. Lett. 9 (1999) 291-294
5. Fletcher S.R., Burkamp F., Blurton P., Cheng S.K.F., Clarkson R., O'Connor D., Spinks D., Tudge M., van Niel M.B., Patel S., Chapman K., Marwood R., Shepeard S., Bentley G., Cook G.P., Bristow L.J., Castro J.L., Hutson P.H., and MacLeod A.M. J. Med. Chem. 45 (2002) 492-503
6. Harsanyi, K.; Szabadkai, I.; Borza, I.; Karpati, E.; Kiss, B.; Pellionisz, M.; Farkas, S.; Horvath, C.; Csomor, K.; Lapis, E.; Laszlovszky, I.; Szabo, S.; Kis-Varga, A.; Laszy, J.; Gere, A. WO9737630, 1997.
7. Yamato M., Hashigaki K., Tsutsumi A., and Tasaka K. Chem. Pharm. Bull. 29 (1981) 3494-3498
8. Le Bourdonnec B., Windh R.T., Ajello C.W., Leister L.K., Gu M., Chu G.-H., Tuthill P.A., Barker W.M., Koblish M., Wiant D.D., Graczyk T.M., Belanger S., Cassel J.A., Feschenko M.S., Brogdon B.L., Smith S.A., Christ D.D., Derelanko M.J., Kutz S., Little P.J., DeHaven R.N., DeHaven-Hudkins D.L., and Dolle R.E. J. Med. Chem. 51 (2008) 5893-5896
9. Kabbe H.J. Synthesis (1978) 886-887
10. Chandrasekhar S., Vijeender K., and Reddy K.V. Tetrahedron Lett. 46 (2005) 6991-6993
11. Sebhat I.K., Lai Y., Barakat K., Ye Z., Tang R., Kalyani R.N., Vongs A., MacNeil T., Weinberg D.H., Cabello M.A., Maroto M., Teran A., Fomg T.M., Van der Ploeg L.H.T., Patchett A.A., and Nargund R.P. Bioorg. Med. Chem. Lett. 17 (2007) 5720-5723
12. The spiroindane ring system and spirocycle 14 have been reported in the literature:
13. Chambers M.S., Baker R., Billington D.C., Knight A.K., Middlemiss D.N., and Wong E.H.F. J. Med. Chem. 35 (1992) 2033-2039
14. Makings, L. R.; Garcia-Guzman Blanco, M.; Hurley, D. J.; Drutu, I.; Raffai, G; Bergeron, D. J.; Nakatani, A.; Termin, A. P.; Silinas, A. WO2006023852, 2006.
15. Dolle, R. E.; Le Bourdonnec, B.; Chu, G.-H. WO2006105442, 2006.