A flexible synthetic route to isoxazolidine β-proline analogs

Tetrahedron

Volumn 65, Issue 16, 2009, Pages 3305-3313

  Buhrlage, Sara J ^a   Chen, Bin ^a   Mapp, Anna K ^a  

^a UNIVERSITY OF MICHIGAN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ISOXAZOLIDINE BETA PROLINE DERIVATIVE; ISOXAZOLIDINE DERIVATIVE; OLIGOMER; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; ENANTIOMER; PRIORITY JOURNAL; REACTION ANALYSIS; SOLID; STEREOISOMERISM; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 62049083153     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2008.12.062     Document Type: Article

References (38)

1. Gellman S.H. Acc. Chem. Res. 31 (1999) 173-180
2. Hill D.J., Mio M.J., Prince R.B., Hughes T.S., and Moore J.S. Chem. Rev. 101 (2001) 3893-4012
3. Bautista A.D., Craig C.J., Harker E.A., and Schepartz A. Curr. Opin. Chem. Biol. 11 (2007) 685-692
4. Seebach D., Hook D.F., and Glattli A. Biopolymers 84 (2006) 23-37
5. Seebach D.M., and Matthews J.L. Chem. Commun. (1997) 2015-2022
6. Cheng R.P., Gellman S.H., and DeGrado W.F. Chem. Rev. 101 (2001) 3219-3232
7. Qiu J.X., Petersson E.J., Matthews E.E., and Schepartz A. J. Am. Chem. Soc. 128 (2006) 11338-11339
8. Raguse T.L., Lai J.R., LePlae P.R., and Gellman S.H. Org. Lett. 3 (2001) 3963-3966
9. Cheng R.P., and DeGrado W.F. J. Am. Chem. Soc. 124 (2002) 11564-11565
10. Goodman J.L., Molski M.A., Qiu J., and Schepartz A. Chembiochem 9 (2008) 1576-1578
11. Goodman J.L., Petersson E.J., Daniels D.S., Qiu J.X., and Schepartz A. J. Am. Chem. Soc. 129 (2007) 14746-14751
12. Daniels D.S., Petersson E.J., Qiu J.X., and Schepartz A. J. Am. Chem. Soc. 129 (2007) 1532-1533
13. Larsson O.M., Thorbek P., Krogsgaard-Larsen P., and Schousboe A. J. Neurochem. 37 (1981) 1509-1516
14. Mitsumori S., Zhang H., Ha-Yeon Cheong P., Houk K.N., Tanaka F., and Barbas III C.F. J. Am. Chem. Soc. 128 (2006) 1040-1041
15. Zhang H., Mitsumori S., Utsumi N., Imai M., Garcia-Delgado N., Mifsud M., Albertshofer K., Cheong P.H., Houk K.N., Tanaka F., and Barbas III C.F. J. Am. Chem. Soc. 130 (2008) 875-886
16. Min J.Z., Toyo'oka T., Kato M., and Fukushima T. Biomed. Chromatogr. 19 (2005) 43-50
17. Huck B.R., Langenhan J.M., and Gellman S.H. Org. Lett. 1 (1999) 1717-1720
18. Sandvoss L.M., and Carlson H.A. J. Am. Chem. Soc. 125 (2003) 15855-15862
19. Huck B.R., Fisk J.D., Guzei I.A., Carlson H.A., and Gellman S.H. J. Am. Chem. Soc. 125 (2003) 9035-9037
20. Huck B.R., and Gellman S.H. J. Org. Chem. 70 (2005) 3353-3362
21. Martin S.F., and Dupre B. Tetrahedron Lett. 24 (1983) 1337-1340
22. Kozikowski A.P. Acc. Chem. Res. 17 (1984) 410-416
23. Muri D., Lohse-Fraefel N., and Carreira E.M. Angew. Chem., Int. Ed. 44 (2005) 4036-4038
24. Curran D. J. Am. Chem. Soc. 104 (1982) 4024-4026
25. Fader L.D., and Carreira E.M. Org. Lett. 6 (2004) 2485-2488
26. Curran D.P., and Zhang J.C. J. Chem. Soc., Perkin Trans. 1 (1991) 2613-2625
27. Asaoka M., Abe M., Mukuta T., and Takei H. Chem. Lett. (1982) 215-218
28. Fuller A.A., Chen B., Minter A.R., and Mapp A.K. J. Am. Chem. Soc. 127 (2005) 5376-5383
29. Minter A.R., Fuller A.A., and Mapp A.K. J. Am. Chem. Soc. 125 (2003) 6846-6847
30. Bode J.W., Fraefel N., Muri D., and Carreira E.M. Angew. Chem., Int. Ed. 40 (2001) 2082-2085
31. Kanemasa S., Nishiuchi M., Kamimura A., and Hori K.J. J. Am. Chem. Soc. 116 (1994) 2324-2339
32. Davoille R.J., Rutherford D.T., and Christie S.D.R. Tetrahdron Lett. 41 (2000) 1255-1259
33. Wang J.C., and Just G. J. Org. Chem. 64 (1999) 8090-8097
34. Minter A.R., Brennan B.B., and Mapp A.K. J. Am. Chem. Soc. 126 (2004) 10504-10505
35. Buhrlage S.J., Brennan B.B., Minter A.R., and Mapp A.K. J. Am. Chem. Soc. 127 (2005) 12456-12457
36. Casey, R. J.; Desaulniers, J. P.; Hojfeldt, J. W.; Mapp, A. K. Bioorg. Med. Chem., in press, doi:10.1016/j.bmc.2008.02.045.
37. Pangborn A.B., Giardello M.A., Grubbs R.H., Rosen R.K., and Timmers F.J. Organometallics 15 (1996) 1518-1520
38. Still W.C., Kahn M., and Mitra A. J. Org. Chem. 43 (1978) 2923-2925