-
1
-
-
38549093011
-
-
For reviews, see: (a)
-
For reviews, see: (a) Wymann, M. P.; Schneiter, R. Nat. Rev. Mol. Cell Biol. 2008, 9, 162.
-
(2008)
Nat. Rev. Mol. Cell Biol.
, vol.9
, pp. 162
-
-
Wymann, M.P.1
Schneiter, R.2
-
3
-
-
0035942309
-
-
(c) Hannun, Y. A.; Luberto, C.; Argraves, K. M. Biochemistry 2001, 40, 4893.
-
(2001)
Biochemistry
, vol.40
, pp. 4893
-
-
Hannun, Y.A.1
Luberto, C.2
Argraves, K.M.3
-
4
-
-
0033152727
-
-
(d) Kolter, T.; Sandhoff, K. Angew. Chem., Int. Ed. 1999, 38, 1532.
-
(1999)
Angew. Chem., Int. Ed.
, vol.38
, pp. 1532
-
-
Kolter, T.1
Sandhoff, K.2
-
5
-
-
70349091281
-
-
For a review of SMase, see
-
For a review of SMase, see: Montes, L. R.; Goni, F. M.; Alonso, A. Sphingolipids Cell Funct. 2006, 53.
-
(2006)
Sphingolipids Cell Funct.
, pp. 53
-
-
Montes, L.R.1
Goni, F.M.2
Alonso, A.3
-
6
-
-
38349158920
-
-
For select examples on the preparation of SMase inhibitors, see: (a)
-
For select examples on the preparation of SMase inhibitors, see: (a) Kornhuber, J.; Tripal, P.; Reichel, M.; Terfloth, L.; Bleich, S.; Wiltfanf, J.; Gulbins, E. J. Med. Chem. 2008, 51, 219.
-
(2008)
J. Med. Chem.
, vol.51
, pp. 219
-
-
Kornhuber, J.1
Tripal, P.2
Reichel, M.3
Terfloth, L.4
Bleich, S.5
Wiltfanf, J.6
Gulbins, E.7
-
8
-
-
31444453971
-
-
references cited therein
-
(c) Wascholowski, V.; Giannis, A. Angew. Chem., Int. Ed. 2006, 45, 827 and references cited therein.
-
(2006)
Angew. Chem., Int. Ed.
, vol.45
, pp. 827
-
-
Wascholowski, V.1
Giannis, A.2
-
11
-
-
0009579274
-
-
(a) Yokomatsu, T.; Takechi, H.; Akiyama, T.; Shibuya, S.; Kominato, T.; Soeda, S.; Shimeno, H. Bioorg. Med. Chem. Lett. 2001, 11, 1227.
-
(2001)
Bioorg. Med. Chem. Lett.
, vol.11
, pp. 1227
-
-
Yokomatsu, T.1
Takechi, H.2
Akiyama, T.3
Shibuya, S.4
Kominato, T.5
Soeda, S.6
Shimeno, H.7
-
12
-
-
0037212776
-
-
(b) Yokomatsu, T.; Murano, T.; Akiyama, T.; Koizumi, J.; Shibuya, S.; Tsuji, Y.; Soeda, S.; Shimeno, H. Bioorg. Med. Chem. Lett. 2003, 13, 229.
-
(2003)
Bioorg. Med. Chem. Lett.
, vol.13
, pp. 229
-
-
Yokomatsu, T.1
Murano, T.2
Akiyama, T.3
Koizumi, J.4
Shibuya, S.5
Tsuji, Y.6
Soeda, S.7
Shimeno, H.8
-
13
-
-
33644904578
-
-
Katsumura and co-workers independently reported that the DFMP analogue of sphingomyelin inhibits SMase competitively, see
-
Katsumura and co-workers independently reported that the DFMP analogue of sphingomyelin inhibits SMase competitively, see: Hakogi, T.; Yamamoto, T.; Fujii, S.; Ikeda, K.; Katsumura, S. Tetrahedron Lett. 2006, 47, 2627.
-
(2006)
Tetrahedron Lett.
, vol.47
, pp. 2627
-
-
Hakogi, T.1
Yamamoto, T.2
Fujii, S.3
Ikeda, K.4
Katsumura, S.5
-
14
-
-
54849404494
-
-
(a) Soeda, S.; Sakata, A.; Ochiai, T.; Yasuda, K.; Shimeno, H.; Toda, A.; Eyanagi, R.; Hikishima, S.; Yokomatsu, T.; Shibuya, S. Curr. Drug Therapy 2008, 3, 218.
-
(2008)
Curr. Drug Therapy
, vol.3
, pp. 218
-
-
Soeda, S.1
Sakata, A.2
Ochiai, T.3
Yasuda, K.4
Shimeno, H.5
Toda, A.6
Eyanagi, R.7
Hikishima, S.8
Yokomatsu, T.9
Shibuya, S.10
-
15
-
-
3042599022
-
-
(b) Soeda, S.; Tsuji, Y.; Ochiai, T.; Mishima, K.; Iwasaki, K.; Fujiwara, M.; Yokomatsu, T.; Murano, T.; Shibuya, S.; Shimeno, H. Neurochem. Int. 2004, 45, 619.
-
(2004)
Neurochem. Int.
, vol.45
, pp. 619
-
-
Soeda, S.1
Tsuji, Y.2
Ochiai, T.3
Mishima, K.4
Iwasaki, K.5
Fujiwara, M.6
Yokomatsu, T.7
Murano, T.8
Shibuya, S.9
Shimeno, H.10
-
16
-
-
34547659848
-
-
(c) Sakata, A.; Ochiai, T.; Shimeno, H.; Hikishima, S.; Yokomatsu, T.; Shibuya, S.; Toda, A.; Eyanagi, R.; Soeda, S. Immunology 2007, 122, 54.
-
(2007)
Immunology
, vol.122
, pp. 54
-
-
Sakata, A.1
Ochiai, T.2
Shimeno, H.3
Hikishima, S.4
Yokomatsu, T.5
Shibuya, S.6
Toda, A.7
Eyanagi, R.8
Soeda, S.9
-
17
-
-
34248666988
-
-
(d) Sakata, A.; Yasuda, K.; Ochiai, T.; Shimeno, H.; Hikishima, S.; Yokomatsu, T.; Shibuya, S.; Soeda, S. Cellular Immunol. 2007, 245, 24.
-
(2007)
Cellular Immunol.
, vol.245
, pp. 24
-
-
Sakata, A.1
Yasuda, K.2
Ochiai, T.3
Shimeno, H.4
Hikishima, S.5
Yokomatsu, T.6
Shibuya, S.7
Soeda, S.8
-
18
-
-
0028814196
-
-
(a) Otaka, A.; Miyoshi, K.; Burke, T. R., Jr.; Roller, P. P.; Kurobe, H.; Tamamura, H.; Fujii, N. Tetrahedron Lett. 1995, 36, 927.
-
(1995)
Tetrahedron Lett.
, vol.36
, pp. 927
-
-
Otaka, A.1
Miyoshi, K.2
Burke Jr., T.R.3
Roller, P.P.4
Kurobe, H.5
Tamamura, H.6
Fujii, N.7
-
19
-
-
0029885050
-
-
(b) Berkowitz, D. B.; Eggen, M.; Shen, Q.; Shoemarker, R. K. J. Org. Chem. 1996, 61, 4666.
-
(1996)
J. Org. Chem.
, vol.61
, pp. 4666
-
-
Berkowitz, D.B.1
Eggen, M.2
Shen, Q.3
Shoemarker, R.K.4
-
20
-
-
0026537894
-
-
Martin, S.M.; Dean, D.W.; Wagman, A.S. Tetrahedron Lett. 1992, 33, 1839.
-
(1992)
Tetrahedron Lett.
, vol.33
, pp. 1839
-
-
Martin, S.M.1
Dean, D.W.2
Wagman, A.S.3
-
21
-
-
36949039981
-
-
(a) Ozturk, T.; Ertas, E.; Mert, O. Chem. Rev. 2007, 107, 5210.
-
(2007)
Chem. Rev.
, vol.107
, pp. 5210
-
-
Ozturk, T.1
Ertas, E.2
Mert, O.3
-
24
-
-
0030249820
-
-
Yokomatsu, T.; Sato, M.; Shibuya, S. Tetrahedron: Asymmetry 1996, 7, 2743.
-
(1996)
Tetrahedron: Asymmetry
, vol.7
, pp. 2743
-
-
Yokomatsu, T.1
Sato, M.2
Shibuya, S.3
-
25
-
-
0344926605
-
-
Murano, T.; Yuasa, Y.; Kobayakawa, H.; Yokomatsu, T.; Shibuya, S. Tetrahedron 2003, 59, 10223.
-
(2003)
Tetrahedron
, vol.59
, pp. 10223
-
-
Murano, T.1
Yuasa, Y.2
Kobayakawa, H.3
Yokomatsu, T.4
Shibuya, S.5
-
26
-
-
70349131018
-
-
note
-
Yields refers to those from crude aldehyde 2 and not optimized.
-
-
-
-
27
-
-
70349083186
-
-
note
-
An accurate yield was not caluculated because of some inseparable impurities included.
-
-
-
-
28
-
-
70349121152
-
-
note
-
For the preparation of amino ketones 5, we have synthesized the Weinreb amide derived from alcohol 11 and examined the reaction with a large excess of vinyl magnesium bromide (THF/0 °C to rt). However, the Weinreb amide was found to be inert to the Grignad reagent under our experimental conditions. In a series of the phosphonothiate analogues, we failed to prepare the correponding carboxylate due to significant decomposition of 12 during oxidation. Therefore, we could not examine the reactivity of the Weinreb amide, derived from alcohol 12, to the Grignard reagent.
-
-
-
-
29
-
-
0026730481
-
-
To obtain the required amino alcohol derivertives in a stereoselective manner, an alternative method may be available on the basis of sequential DIBAL-mediated reduction and alkylation with a Grignard reaction toward amino esters in one pot. (a)
-
To obtain the required amino alcohol derivertives in a stereoselective manner, an alternative method may be available on the basis of sequential DIBAL-mediated reduction and alkylation with a Grignard reaction toward amino esters in one pot. (a) Polt, R.; Peterson, M. A.; DeYong, L. J. Org. Chem. 1992, 57, 5469.
-
(1992)
J. Org. Chem.
, vol.57
, pp. 5469
-
-
Polt, R.1
Peterson, M.A.2
DeYong, L.3
-
30
-
-
0025003890
-
-
However, in the present studies, we focused on the alkylation- oxidationreduction sequence starting from aldehydes 1 and 2
-
(b) Polt, R.; Peterson, M. A. Tetraherdon Lett. 1990, 31, 4985. However, in the present studies, we focused on the alkylation-oxidationreduction sequence starting from aldehydes 1 and 2.
-
(1990)
Tetraherdon Lett.
, vol.31
, pp. 4985
-
-
Polt, R.1
Peterson, M.A.2
-
31
-
-
0037154749
-
-
(a) Hoffman, R. V.; Maslouh, N.; Cervantes-Lee, F. J. Org. Chem. 2002, 67, 1045.
-
(2002)
J. Org. Chem.
, vol.67
, pp. 1045
-
-
Hoffman, R.V.1
Maslouh, N.2
Cervantes-Lee, F.3
-
32
-
-
58049193072
-
-
(b) Davis, F. A.; Gaspari, P. M.; Nolt, B. M.; Xu, P. J. Org. Chem. 2008, 73, 9619.
-
(2008)
J. Org. Chem.
, vol.73
, pp. 9619
-
-
Davis, F.A.1
Gaspari, P.M.2
Nolt, B.M.3
Xu, P.4
-
33
-
-
0037065304
-
-
Lopin, C.; Gautier, A.; Gouhier, G.; Piettre, S. R. J. Am. Chem. Soc. 2002, 124, 14668.
-
(2002)
J. Am. Chem. Soc.
, vol.124
, pp. 14668
-
-
Lopin, C.1
Gautier, A.2
Gouhier, G.3
Piettre, S.R.4
|