Synthesis and chemical diversity analysis of bicyclo[3.3.1]non-3-en-2-ones

Tetrahedron

Volumn 66, Issue 31, 2010, Pages 5852-5862

  Hammill, Jared T ^a   Contreras García, Julia ^b   Virshup, Aaron M ^b   Beratan, David N ^a,b   Yang, Weitao ^a,b   Wipf, Peter ^a  

^a UNIVERSITY OF PITTSBURGH   (United States)

^b DUKE UNIVERSITY   (United States)

Author keywords

Bicyclo 3.3.1 nonenones; Chemical diversity analysis; Epoxyketone rearrangement; Ring opening

Indexed keywords

BICYCLO[3.3.1]NON 3 EN 2 ONE DERIVATIVE; EPOXIDE; GYMNASTATIN F; GYMNASTATIN G; IODINE; NATURAL PRODUCT; PHENOL DERIVATIVE; THIOPHENOL; UNCLASSIFIED DRUG;

ALDOL REACTION; ARTICLE; CHEMICAL ANALYSIS; MICROWAVE RADIATION; NUCLEAR MAGNETIC RESONANCE; OXIDATION; PHYSICAL CHEMISTRY; PRIORITY JOURNAL; ROOM TEMPERATURE; SYNTHESIS;

EID: 77955471052     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2010.04.112     Document Type: Article

References (51)

1. http://omics.org/index.php/Main-Page
2. http://en.wikipedia.org/wiki/Signaling-pathway
3. See also: P. Wipf, D. Arnold, K. Carter, S. Dong, P.A. Johnston, E. Sharlow, J.S. Lazo, and D. Huryn Curr. Top. Med. Chem 9 2009 1194 http://mli.nih.gov/mli/ and references cited therein
4. http://www.nigms.nih.gov/Initiatives/CMLD See, for example:
5. J.G. Pierce, D. Kasi, M. Fushimi, A. Cuzzupe, and P. Wipf J. Org. Chem. 73 2008 7807
6. P. Wipf, S. Werner, G.H.C. Woo, C.R.J. Stephenson, M.A.A. Walczak, C.M. Coleman, and L.A. Twining Tetrahedron 61 2005 11488
7. http://mlsmr.glpg.com/MLSMR-HomePage/
8. http://pubchem.ncbi.nlm.nih.gov/
9. J.M. Ostresh, G.H. Husar, S.E. Blondelle, P.A. Dorner, R.A. Weber, and R.A. Houghten Proc. Natl. Acad. Sci. U.S.A. 91 1994 11138
10. H.E. Blackwell, L. Perez, R.A. Stavenger, J.A. Tallarico, E. Cope Eatough, M.A. Foley, and S.L. Schreiber Chem. Biol. 8 2001 1167
11. P. Wipf, C.R.J. Stephenson, and M.A.A. Walczak Org. Lett. 6 2004 3009
12. Anon. Nat. Rev. Drug Discov. 3 2004 375
13. R. Van Deursen, and J.-L. Reymond ChemMedChem 2 2007 636
14. S. Wetzel, A. Schuffenhauer, S. Roggo, P. Ertl, and H. Waldmann Chimia 61 2007 355
15. J. Rosen, J. Gottfries, S. Muresan, A. Backlund, and T.I. Oprea J. Med. Chem. 52 2009 1953
16. P.D. Leeson, A.M. Davis, and J. Steele Drug Discovery Today 1 2004 189
17. R.S. Bohacek, C. McMartin, and W.C. Guida Med. Res. Rev. 16 1996 3
18. L.C. Blum, and J.-L. Reymond J. Am. Chem. Soc. 131 2009 8732
19. C.M. Dobson Nature 432 2004 824
20. J. Clardy, and C. Walsh Nature 432 2004 829
21. D.S. Tan Nat. Chem. Biol. 1 2005 74
22. A.L. Jones, and J.K. Snyder Org. Lett. 12 2010 1592 and references cited therein
23. T. Amagata, K. Minoura, and A. Numata J. Nat. Prod. 69 2006 1384
24. T. Amagata, M. Tanaka, T. Yamada, K. Minoura, and A. Numata J. Nat. Prod. 71 2008 340
25. P. Wipf, Y. Kim, and P.C. Fritch J. Org. Chem. 58 1993 7195
26. P. Wipf, P. Jeger, and Y. Kim Bioorg. Med. Chem. Lett. 8 1998 351
27. For other approaches to bicyclo[3.3.1]nonanes, see: R. Ciochina, and R.B. Grossman Chem. Rev. 106 2006 3963
28. D.R. Siegel, and S.J. Danishefsky J. Am. Chem. Soc. 128 2006 1048
29. A. Kuramochi, H. Usuda, K. Yamatsugu, M. Kanai, and M. Shibasaki J. Am. Chem. Soc. 127 2005 14200
30. S. Bhunia, K.-C. Wang, and R.-S. Liu Angew. Chem., Int. Ed. 47 2008 5063
31. Y.-L. Zhao, L. Chen, S.-C. Yang, C. Tian, and Q. Liu J. Org. Chem. 74 2009 5622
32. D. Wang, and W.E. Crowe Org. Lett. 12 2010 1232 and references cited therein
33. V.V. Zhdankin ARKIVOC 2009 1
34. R.M. Moriarty J. Org. Chem. 70 2005 2893
35. S. Rodriguez, and P. Wipf Synthesis 2004 2767
36. P. Wipf, S.M. Lynch, A. Birmingham, G. Tamayo, A. Jimenez, N. Campos, and G. Powis Org. Biomol. Chem. 2 2004 1651
37. P. Wipf, J.-K. Jung, S. Rodriguez, and J.S. Lazo Tetrahedron 57 2001 283
38. A. McKillop, L. McLaren, R.J. Watson, R.J.K. Taylor, and N. Lewis Tetrahedron Lett. 34 1993 5519
39. A.V. Rama Rao, M.K. Gurjar, and P.A. Sharma Tetrahedron Lett. 32 1991 6613
40. A. McKillop, R. Taylor, R. Watson, and N. Lewis J. Chem. Soc. 1992 1589
41. A. McKillop, R.J.K. Taylor, R.J. Watson, and L. Norman Synlett 1992 1005
42. Kim, Y. Ph.D. Thesis, University of Pittsburgh, 1995.
43. M. Yu, and S.J. Danishefsky J. Am. Chem. Soc. 130 2008 2783
44. G. Wells, J.M. Berry, T.D. Bradshaw, A.M. Burger, A. Seaton, B. Wang, A.D. Westwell, and M.F. Stevens J. Med. Chem. 46 2003 532
45. J. Rosen, A. Loevgren, T. Kogej, S. Muresan, J. Gottfries, and A. Backlund J. Comput.-Aided Mol. Des. 23 2009 253
46. OEChem, version 1.3.4 2005 OpenEye Scientific Software, Santa Fe, NM, USA www.eyesopen.com
47. Instant JChem was used for structure database management, search and prediction, Instant JChem 5.3.1, 2010, ChemAxon (http://www.chemaxon.com ).
48. C.A. Lipinski, F. Lombardo, B.W. Dominya, and P.J. Feeney Adv. Drug Delivery Rev. 23 1997 3
49. T.I. Oprea, A.M. Davis, S.J. Teague, and P.D. Leeson J. Chem. Inf. Comput. Sci. 41 2001 1308
50. E. Perola J. Med. Chem. 53 2010 2986
51. 2 before the dimethylsulfide is added.