-
2
-
-
0000083882
-
-
Blakley, R. L., Benkovic, S. J., Eds.; Wiley: New York
-
McGuire, J. J.; Coward, J. K. In Folates and Pterins; Blakley, R. L., Benkovic, S. J., Eds.; Wiley: New York, 1984; Vol. 1, pp 135-190.
-
(1984)
Folates and Pterins
, vol.1
, pp. 135-190
-
-
McGuire, J.J.1
Coward, J.K.2
-
4
-
-
0037455808
-
-
Liani, E.; Rothem, L.; Bunni, M. A.; Smith, C. A.; Jansen, G.; Assaraf, Y. G. Int. J. Cancer 2003, 103, 587-599.
-
(2003)
Int. J. Cancer
, vol.103
, pp. 587-599
-
-
Liani, E.1
Rothem, L.2
Bunni, M.A.3
Smith, C.A.4
Jansen, G.5
Assaraf, Y.G.6
-
5
-
-
0030954945
-
-
Roy, K; Egan, M. G.; Sirlin, S.; Sirotnak, F. M. J. Biol. Chem. 1997, 272, 6903-6908.
-
(1997)
J. Biol. Chem.
, vol.272
, pp. 6903-6908
-
-
Roy, K.1
Egan, M.G.2
Sirlin, S.3
Sirotnak, F.M.4
-
7
-
-
0032126162
-
-
Tsukamoto, T.; Haile, W. H.; McGuire, J. J.; Coward, J. K. Arch. Biochem. Biophys. 1998, 355, 109-118.
-
(1998)
Arch. Biochem. Biophys.
, vol.355
, pp. 109-118
-
-
Tsukamoto, T.1
Haile, W.H.2
McGuire, J.J.3
Coward, J.K.4
-
8
-
-
0035958480
-
-
Valiaeva, N.; Hartley, D.; Konno, T.; Coward, J. K. J. Org. Chem. 2001, 66, 5146-5154.
-
(2001)
J. Org. Chem.
, vol.66
, pp. 5146-5154
-
-
Valiaeva, N.1
Hartley, D.2
Konno, T.3
Coward, J.K.4
-
9
-
-
0021339180
-
-
Rosowsky, A.; Forsch, R. A.; Freisheim, J. H.; Moran, R. G.; Wick, M. J. Med. Chem. 1984, 27, 600-604.
-
(1984)
J. Med. Chem.
, vol.27
, pp. 600-604
-
-
Rosowsky, A.1
Forsch, R.A.2
Freisheim, J.H.3
Moran, R.G.4
Wick, M.5
-
10
-
-
0011821153
-
-
Goldman, I. D., Ed.; Praeger Publishers: New York
-
Cichowicz, D. J.; Cook, J.; George, S.; Shane, B. In Proceedings of the Second Workshop on Folyl- and Antifoyl-polyglutamates; Goldman, I. D., Ed.; Praeger Publishers: New York, 1985; pp 7-13.
-
(1985)
Proceedings of the Second Workshop on Folyl- and Antifoyl-polyglutamates
, pp. 7-13
-
-
Cichowicz, D.J.1
Cook, J.2
George, S.3
Shane, B.4
-
11
-
-
0021912292
-
-
Rosowsky, A.; Freisheim, J. H.; Bader, H.; Forsch, R. A.; Susten, S. S.; Cucchi, C. A.; Frei, E. J. Med. Chem. 1985, 28, 660-667.
-
(1985)
J. Med. Chem.
, vol.28
, pp. 660-667
-
-
Rosowsky, A.1
Freisheim, J.H.2
Bader, H.3
Forsch, R.A.4
Susten, S.S.5
Cucchi, C.A.6
Frei, E.7
-
12
-
-
0022508774
-
-
Rosowsky, A.; Freisheim, J. H.; Moran, R. G.; Solan, V. C.; Bader, H.; Wright, J. E.; Radike-Smith, M. J. Med. Chem. 1986, 29, 655-660.
-
(1986)
J. Med. Chem.
, vol.29
, pp. 655-660
-
-
Rosowsky, A.1
Freisheim, J.H.2
Moran, R.G.3
Solan, V.C.4
Bader, H.5
Wright, J.E.6
Radike-Smith, M.7
-
13
-
-
0023493361
-
-
Rosowsky, A.; Moran, R. G.; Freisheim, J. H.; Bader, H.; Forsch, R. A.; Solan, V. C. NCI Monogr. 1987, 5, 145-152.
-
(1987)
NCI Monogr.
, vol.5
, pp. 145-152
-
-
Rosowsky, A.1
Moran, R.G.2
Freisheim, J.H.3
Bader, H.4
Forsch, R.A.5
Solan, V.C.6
-
14
-
-
0023759004
-
-
Rosowsky, A.; Forsch, R. A.; Moran, R. G.; Kohler, W.; Freisheim, J. H. J. Med. Chem. 1988, 31, 1326-1331.
-
(1988)
J. Med. Chem.
, vol.31
, pp. 1326-1331
-
-
Rosowsky, A.1
Forsch, R.A.2
Moran, R.G.3
Kohler, W.4
Freisheim, J.H.5
-
15
-
-
0024399263
-
-
Patil, S. A.; Shane, B.; Freisheim, J. H.; Singh, S. K.; Hynes, J. B. J. Med. Chem. 1989, 32, 1559-1565.
-
(1989)
J. Med. Chem.
, vol.32
, pp. 1559-1565
-
-
Patil, S.A.1
Shane, B.2
Freisheim, J.H.3
Singh, S.K.4
Hynes, J.B.5
-
16
-
-
0026539605
-
-
Hynes, J. B.; Singh, S. K.; Fetzer, O.; Shane, B. J. Med. Chem. 1992, 35, 4078-4085.
-
(1992)
J. Med. Chem.
, vol.35
, pp. 4078-4085
-
-
Hynes, J.B.1
Singh, S.K.2
Fetzer, O.3
Shane, B.4
-
17
-
-
0030891198
-
-
Shih, C.; Chen, V. J.; Gossett, L. S.; Gates, S. B.; Mackellar, W. C.; Habeck, L. L.; Shackelford, K. A.; Mendelsohn, L. G.; Soose, D. J.; Patel, V. F.; Andis, S. L.; Bewley, J. R.; Rayl, E. A.; Moroson, B. A.; Beardsley, G. P.; Kohler, W.; Ratnam, M.; Schultz, R. M. Cancer Res. 1997, 57, 1116-1123.
-
(1997)
Cancer Res.
, vol.57
, pp. 1116-1123
-
-
Shih, C.1
Chen, V.J.2
Gossett, L.S.3
Gates, S.B.4
Mackellar, W.C.5
Habeck, L.L.6
Shackelford, K.A.7
Mendelsohn, L.G.8
Soose, D.J.9
Patel, V.F.10
Andis, S.L.11
Bewley, J.R.12
Rayl, E.A.13
Moroson, B.A.14
Beardsley, G.P.15
Kohler, W.16
Ratnam, M.17
Schultz, R.M.18
-
18
-
-
0033622009
-
-
Galivan, J.; Ryan, T. J.; Chave, K.; Rhee, M.; Yao, R.; Yin, D. Pharmacol. Ther. 2000, 85, 207-215.
-
(2000)
Pharmacol. Ther.
, vol.85
, pp. 207-215
-
-
Galivan, J.1
Ryan, T.J.2
Chave, K.3
Rhee, M.4
Yao, R.5
Yin, D.6
-
19
-
-
0000921074
-
-
Jackman, A. L., Ed.; Humana Press: Totowa, New Jersey
-
Jansen, G. In Antifolate Drugs in Cancer Therapy; Jackman, A. L., Ed.; Humana Press: Totowa, New Jersey, 1999; pp 293-321.
-
(1999)
Antifolate Drugs in Cancer Therapy
, pp. 293-321
-
-
Jansen, G.1
-
20
-
-
0024285812
-
-
Banerjee, R. V.; Shane, B.; McGuire, J. J.; Coward, J. K. Biochemistry 1988, 27, 9062-9070.
-
(1988)
Biochemistry
, vol.27
, pp. 9062-9070
-
-
Banerjee, R.V.1
Shane, B.2
McGuire, J.J.3
Coward, J.K.4
-
21
-
-
0037299779
-
-
McGuire, J. J.; Haile, W. H.; Valiaeva, N.; Bartley, D.; J., G.; Coward, J. K. Biochem. Pharmacol. 2003, 65, 315-318.
-
(2003)
Biochem. Pharmacol.
, vol.65
, pp. 315-318
-
-
McGuire, J.J.1
Haile, W.H.2
Valiaeva, N.3
Bartley, D.4
Coward, J.K.5
-
23
-
-
0021128805
-
-
Thottathil, J. K.; Przybyla, C. A.; Moniot, J. L. Tetrahedron Lett. 1984, 25, 4737-4740.
-
(1984)
Tetrahedron Lett.
, vol.25
, pp. 4737-4740
-
-
Thottathil, J.K.1
Przybyla, C.A.2
Moniot, J.L.3
-
25
-
-
0036499447
-
-
Liu, X.; Hu, E.; Tian, X.; Mazur, A.; Ebetino, F. H. J. Organomet. Chem. 2002, 646, 212-222.
-
(2002)
J. Organomet. Chem.
, vol.646
, pp. 212-222
-
-
Liu, X.1
Hu, E.2
Tian, X.3
Mazur, A.4
Ebetino, F.H.5
-
26
-
-
0032567399
-
-
Zeng, B.; Wong, K. K; Pompliano, D. L.; Reddy, S.; Tanner, M. E. J. Org. Chem. 1998, 63, 10081-10086.
-
(1998)
J. Org. Chem.
, vol.63
, pp. 10081-10086
-
-
Zeng, B.1
Wong, K.K.2
Pompliano, D.L.3
Reddy, S.4
Tanner, M.E.5
-
27
-
-
0034710712
-
-
Jones, P. B.; Parrish, N. M.; Houston, T. A.; Stapon, A.; Bansal, N. P.; Dick, J. D.; Townsend, C. A. J. Med. Chem. 2000, 43, 3304-3314.
-
(2000)
J. Med. Chem.
, vol.43
, pp. 3304-3314
-
-
Jones, P.B.1
Parrish, N.M.2
Houston, T.A.3
Stapon, A.4
Bansal, N.P.5
Dick, J.D.6
Townsend, C.A.7
-
28
-
-
0035917376
-
-
An, H.; Wang, T.; Maier, M. A.; Manoharan, M.; Ross, B. S.; Cook, P. D. J. Org. Chem. 2001, 66, 2789-2801.
-
(2001)
J. Org. Chem.
, vol.66
, pp. 2789-2801
-
-
An, H.1
Wang, T.2
Maier, M.A.3
Manoharan, M.4
Ross, B.S.5
Cook, P.D.6
-
29
-
-
33748614351
-
-
Miller, D. J.; Hammond, S. M.; Anderluzzi, D.; Bugg, T. D. H. J. Chem. Soc., Perkins Trans. 1 1998, 1, 131-142.
-
(1998)
J. Chem. Soc., Perkins Trans. 1
, vol.1
, pp. 131-142
-
-
Miller, D.J.1
Hammond, S.M.2
Anderluzzi, D.3
Bugg, T.D.H.4
-
31
-
-
0013120837
-
-
Schollkopf, U.; Busse, U.; Lonsky, R.; Hinrichs, R. Liebigs Ann. Chem. 1986, 2150-2163.
-
(1986)
Liebigs Ann. Chem.
, pp. 2150-2163
-
-
Schollkopf, U.1
Busse, U.2
Lonsky, R.3
Hinrichs, R.4
-
32
-
-
0029080017
-
-
Schick, A.; Kolter, T.; Giannis, A.; Sandhoff, K. Tetrahedron 1995, 51, 11207-11218.
-
(1995)
Tetrahedron
, vol.51
, pp. 11207-11218
-
-
Schick, A.1
Kolter, T.2
Giannis, A.3
Sandhoff, K.4
-
33
-
-
0027433935
-
-
Shapiro, G.; Beuchler, D.; Ojea, V.; Pombo-Villar, E.; Ruiz, M.; Weber, H. P. Tetrahedron Lett. 1993, 34, 6255-6258.
-
(1993)
Tetrahedron Lett.
, vol.34
, pp. 6255-6258
-
-
Shapiro, G.1
Beuchler, D.2
Ojea, V.3
Pombo-Villar, E.4
Ruiz, M.5
Weber, H.P.6
-
34
-
-
0028240870
-
-
Ojea, V.; Ruiz, M.; Shapiro, G.; Pombo-Villar, E. Tetrahedron Lett. 1994, 35, 3273-3276.
-
(1994)
Tetrahedron Lett.
, vol.35
, pp. 3273-3276
-
-
Ojea, V.1
Ruiz, M.2
Shapiro, G.3
Pombo-Villar, E.4
-
35
-
-
0028303642
-
-
Ruiz, M.; Ojea, V.; Shapiro, G.; Weber, H. P.; Pombo-Villar, E. Tetrahedron Lett. 1994, 35, 4551-4554.
-
(1994)
Tetrahedron Lett.
, vol.35
, pp. 4551-4554
-
-
Ruiz, M.1
Ojea, V.2
Shapiro, G.3
Weber, H.P.4
Pombo-Villar, E.5
-
36
-
-
0030570904
-
-
Ojea, V.; Fernandez, M. C.; Ruiz, M.; Quintela, J. M. Tetrahedron Lett. 1996, 37, 5801-5804.
-
(1996)
Tetrahedron Lett.
, vol.37
, pp. 5801-5804
-
-
Ojea, V.1
Fernandez, M.C.2
Ruiz, M.3
Quintela, J.M.4
-
37
-
-
0030990715
-
-
Ojea, V.; Conde, S.; Ruiz, M.; Fernandez, M. C.; Quintela, J. M. Tetrahedron Lett. 1997, 38, 4311-4314.
-
(1997)
Tetrahedron Lett.
, vol.38
, pp. 4311-4314
-
-
Ojea, V.1
Conde, S.2
Ruiz, M.3
Fernandez, M.C.4
Quintela, J.M.5
-
38
-
-
33645184089
-
-
Ph.D. Dissertation, University of Michigan, Ann Arbor, MI
-
Bartley, D. M. Ph.D. Dissertation, University of Michigan, Ann Arbor, MI, 2004.
-
(2004)
-
-
Bartley, D.M.1
-
40
-
-
0003100792
-
-
Voronkov, M. G.; Marmur, L. Z.; Dolgov, O. N.; Pestunovich, V. A.; Pokrovski, E. I.; Popel, Y. I. J. Gen. Chem. USSR 1971, 41, 2005-2008.
-
(1971)
J. Gen. Chem. USSR
, vol.41
, pp. 2005-2008
-
-
Voronkov, M.G.1
Marmur, L.Z.2
Dolgov, O.N.3
Pestunovich, V.A.4
Pokrovski, E.I.5
Popel, Y.I.6
-
42
-
-
0003665253
-
-
Wiley: New York; Collect. Vol.
-
Carrasco, M.; Jones, R. J.; Kamel, S.; Rapoport, H.; Truong, T. In Organic Syntheses; Wiley: New York, 1998; Collect. Vol. IX, pp 63-66.
-
(1998)
Organic Syntheses
, vol.9
, pp. 63-66
-
-
Carrasco, M.1
Jones, R.J.2
Kamel, S.3
Rapoport, H.4
Truong, T.5
-
43
-
-
33645175124
-
-
note
-
The checkers of the Organic Synthesis procedure also reported seeing a large amount of rearrangement but attributed it to the silica gel used during the purification; however, we observed the rearrangement products in the NMR spectra of the crude reaction mixture prior to purification.
-
-
-
-
44
-
-
0000085968
-
-
Barton, D. H. R.; Crich, D.; Herve, Y.; Potier, P.; Thiery, J. Tetrahedron 1985, 41, 4347-4357.
-
(1985)
Tetrahedron
, vol.41
, pp. 4347-4357
-
-
Barton, D.H.R.1
Crich, D.2
Herve, Y.3
Potier, P.4
Thiery, J.5
-
45
-
-
33645174786
-
-
44 See Supporting Information for details.
-
(1993)
Synthesis
, pp. 1065
-
-
-
46
-
-
33645186988
-
-
note
-
III chemistry proved much more difficult than was anticipated. Compound 16 could easily be converted into the corresponding mesylate or tosylate in good yield by treatment with the corresponding sulfonyl chloride and pyridine. However, the triflate and iodide could be synthesized only in low yield and the resulting product decomposed at room temperature within minutes, presumable through a nonclassical carbocation intermediate. Ultimately, conditions were optimized for synthesis of the corresponding bromide (Table 2). See Supporting Information for details.
-
-
-
-
48
-
-
37049090352
-
-
Xie, Z.; Suemune, H.; Sakai, K. J. Chem. Soc., Chem. Commun. 1987, 838-839.
-
(1987)
J. Chem. Soc., Chem. Commun.
, pp. 838-839
-
-
Xie, Z.1
Suemune, H.2
Sakai, K.3
-
49
-
-
0025793740
-
-
Fang, C.; Ogawa, T.; Suemune, H.; Sakai, K. Tetrahedron: Asymmetry 1991, 2, 389-398.
-
(1991)
Tetrahedron: Asymmetry
, vol.2
, pp. 389-398
-
-
Fang, C.1
Ogawa, T.2
Suemune, H.3
Sakai, K.4
-
53
-
-
33645168644
-
-
note
-
After 18 h at room temperature only a very small amount of product (2%) was observed.
-
-
-
-
54
-
-
0141712450
-
-
Sharpless, K. B.; Amberg, W.; Bennani, Y. L.; Crispino, G. A.; Hartung, J.; Jeong, K.; Kwong, H.; Morikawa, K.; Wang, Z.; Xu, D.; Zhang, X. J. Org. Chem. 1992, 57, 2768-2771.
-
(1992)
J. Org. Chem.
, vol.57
, pp. 2768-2771
-
-
Sharpless, K.B.1
Amberg, W.2
Bennani, Y.L.3
Crispino, G.A.4
Hartung, J.5
Jeong, K.6
Kwong, H.7
Morikawa, K.8
Wang, Z.9
Xu, D.10
Zhang, X.11
-
56
-
-
49549130554
-
-
VanRheenen, V.; Kelly, R. C.; Cha, D. Y. Tetrahedron Lett. 1976, 23, 1973-1976.
-
(1976)
Tetrahedron Lett.
, vol.23
, pp. 1973-1976
-
-
Vanrheenen, V.1
Kelly, R.C.2
Cha, D.Y.3
-
58
-
-
0000518373
-
-
Bessodes, M.; Lomiotis, D.; Antonakis, K. Tetrahedron Lett. 1986, 27, 579-580.
-
(1986)
Tetrahedron Lett.
, vol.27
, pp. 579-580
-
-
Bessodes, M.1
Lomiotis, D.2
Antonakis, K.3
-
60
-
-
33645176814
-
-
Ph.D. Dissertation, University of Michigan, Ann Arbor, MI
-
Alexander, M. D. Ph.D. Dissertation, University of Michigan, Ann Arbor, MI, 2004.
-
(2004)
-
-
Alexander, M.D.1
-
62
-
-
0024832316
-
-
Amri, H.; Rambaud, M.; Villieras, J. Tetrahedron Lett. 1989, 30, 7381-7382.
-
(1989)
Tetrahedron Lett.
, vol.30
, pp. 7381-7382
-
-
Amri, H.1
Rambaud, M.2
Villieras, J.3
-
63
-
-
84972809471
-
-
Drewes, S. E.; Emslie, N. D.; Karodia, N. Synth. Commun. 1990, 20, 1915-1921.
-
(1990)
Synth. Commun.
, vol.20
, pp. 1915-1921
-
-
Drewes, S.E.1
Emslie, N.D.2
Karodia, N.3
-
64
-
-
0030053446
-
-
Jackson, P. F.; Cole, D. C.; Slusher, B. S.; Stetz, S. L.; Ross, L. E.; Donzanti, B. A.; Trainor, D. A. J. Med. Chem. 1996, 39, 619-622.
-
(1996)
J. Med. Chem.
, vol.39
, pp. 619-622
-
-
Jackson, P.F.1
Cole, D.C.2
Slusher, B.S.3
Stetz, S.L.4
Ross, L.E.5
Donzanti, B.A.6
Trainor, D.A.7
-
65
-
-
0342908046
-
-
Erase, S.; Waigell, B.; de Meijere, A. Synthesis 1998, 2, 148-152.
-
(1998)
Synthesis
, vol.2
, pp. 148-152
-
-
Erase, S.1
Waigell, B.2
De Meijere, A.3
-
68
-
-
0035935670
-
-
Jackson, P. F.; Tays, K. L.; Maclin, K. M.; Ko, Y.; Li, W.; Vitharana, D.; Tsukamoto, T.; Stoermer, D.; Lu, X. M.; Wozniak, K.; Slusher, B. S. J. Med. Chem. 2001, 44, 4170-4175.
-
(2001)
J. Med. Chem.
, vol.44
, pp. 4170-4175
-
-
Jackson, P.F.1
Tays, K.L.2
Maclin, K.M.3
Ko, Y.4
Li, W.5
Vitharana, D.6
Tsukamoto, T.7
Stoermer, D.8
Lu, X.M.9
Wozniak, K.10
Slusher, B.S.11
-
70
-
-
33645181268
-
-
Mitusbishi Petrochemical Co. Ltd., Japanese Patent 59152347, 1984
-
Mitusbishi Petrochemical Co. Ltd., Japanese Patent 59152347, 1984.
-
-
-
-
73
-
-
0034002052
-
-
Prabhu, K. R.; Pillarsetty, N.; Gali, H.; Katti, K. V. J. Am. Chem. Soc. 2000, 122, 1554-1555.
-
(2000)
J. Am. Chem. Soc.
, vol.122
, pp. 1554-1555
-
-
Prabhu, K.R.1
Pillarsetty, N.2
Gali, H.3
Katti, K.V.4
-
75
-
-
33645172371
-
-
Gresham, T. L.; Jansen, J. E.; Shaver, F. W.; Frederick, M. R.; Beears, W. L. J. Am. Chem. Soc. 1951, 73, 2345-2347.
-
(1951)
J. Am. Chem. Soc.
, vol.73
, pp. 2345-2347
-
-
Gresham, T.L.1
Jansen, J.E.2
Shaver, F.W.3
Frederick, M.R.4
Beears, W.L.5
-
77
-
-
0029796652
-
-
Gomez-Bengoa, E.; Cuerva, J. M.; Mateo, C.; Echavarren, A. M. J. Am. Chem. Soc. 1996, 118, 8553-8565.
-
(1996)
J. Am. Chem. Soc.
, vol.118
, pp. 8553-8565
-
-
Gomez-Bengoa, E.1
Cuerva, J.M.2
Mateo, C.3
Echavarren, A.M.4
-
78
-
-
0001466340
-
-
Phoenix, S.; Bourque, E.; Deslongchamps, P. Org. Lett. 2000, 2, 4149-4152.
-
(2000)
Org. Lett.
, vol.2
, pp. 4149-4152
-
-
Phoenix, S.1
Bourque, E.2
Deslongchamps, P.3
-
79
-
-
33645178873
-
-
note
-
Subsequent reactions (Scheme 19) were carried out separately on compounds derived from either 64 (A series, even numbers) or 65 (B series, odd numbers).
-
-
-
-
80
-
-
0001597804
-
-
Evans, D. A.; Britton, T. C.; Ellman, J. A. Tetrahedron Lett. 1987, 28, 6141-6144.
-
(1987)
Tetrahedron Lett.
, vol.28
, pp. 6141-6144
-
-
Evans, D.A.1
Britton, T.C.2
Ellman, J.A.3
-
81
-
-
0030662090
-
-
Luo, J.; Smith, M. D.; Lantrip, D. A.; Wang, S.; Fuchs, P. L. J. Am. Chem. Soc. 1997, 119, 10004-10013.
-
(1997)
J. Am. Chem. Soc.
, vol.119
, pp. 10004-10013
-
-
Luo, J.1
Smith, M.D.2
Lantrip, D.A.3
Wang, S.4
Fuchs, P.L.5
|