-
1
-
-
0034628448
-
-
(a) Leung, D.; Abbenante, G.; Fairlie, D. P. J. Med. Chem. 2000, 43, 305.
-
(2000)
J. Med. Chem.
, vol.43
, pp. 305
-
-
Leung, D.1
Abbenante, G.2
Fairlie, D.P.3
-
4
-
-
0001651169
-
-
and references therein
-
For a recent review article, see: Whittaker, M.; Floyd, C. D.; Brown, P.; Geraing, A. J. H. Chem. Rev. 1999, 99, 2735 and references therein.
-
(1999)
Chem. Rev.
, vol.99
, pp. 2735
-
-
Whittaker, M.1
Floyd, C.D.2
Brown, P.3
Geraing, A.J.H.4
-
6
-
-
0346239860
-
-
British Bio-Technology Ltd.; WO 94 21,625
-
Crimmin, M. J.; Beckett, P. R.; Davis, M. H. British Bio-Technology Ltd.; WO 94 21,625; Chem. Abstr. 1995, 122, 188173y.
-
(1995)
Chem. Abstr.
, vol.122
-
-
Crimmin, M.J.1
Beckett, P.R.2
Davis, M.H.3
-
7
-
-
0000885139
-
-
For work on radical addition to fumarates using imides derived from Kemps triacid, see: (a) Stack, J. G.; Curran, D. P.; Geib, S. V.; Rebek, J., Jr.; Ballester, P. J. Am. Chem. Soc. 1992, 114, 7007.
-
(1992)
J. Am. Chem. Soc.
, vol.114
, pp. 7007
-
-
Stack, J.G.1
Curran, D.P.2
Geib, S.V.3
Rebek J., Jr.4
Ballester, P.5
-
8
-
-
0000770656
-
-
For examination of selectivity in radical addition to fumarates and related systems, see: (b) Porter, N. A.; Bruhnke, J. D.; Wu, W.-X.; Rosenstein, I. J.; Breyer, R. A.; McPhail, A. T. J. Am. Chem. Soc. 1992, 114, 7664.
-
(1992)
J. Am. Chem. Soc.
, vol.114
, pp. 7664
-
-
Porter, N.A.1
Bruhnke, J.D.2
Wu, W.-X.3
Rosenstein, I.J.4
Breyer, R.A.5
McPhail, A.T.6
-
9
-
-
0000624737
-
-
(c) Giese, B.; Zehnder, M.; Roth, M.; Zeitz, H.-G. J. Am. Chem. Soc. 1990, 112, 6741.
-
(1990)
J. Am. Chem. Soc.
, vol.112
, pp. 6741
-
-
Giese, B.1
Zehnder, M.2
Roth, M.3
Zeitz, H.-G.4
-
10
-
-
0000600491
-
-
(d) Porter, N. A.; Scott, D. M.; Lacher, B.; Giese, B.; Zeitz, H. G.; Lindner, H. J. J. Am. Chem. Soc. 1989, 111, 8311.
-
(1989)
J. Am. Chem. Soc.
, vol.111
, pp. 8311
-
-
Porter, N.A.1
Scott, D.M.2
Lacher, B.3
Giese, B.4
Zeitz, H.G.5
Lindner, H.J.6
-
11
-
-
0037155527
-
-
(e) Sibi, M. P.; Liu, P.; Ji, J.; Chen. J. J. Org. Chem. 2002, 67, 1738.
-
(2002)
J. Org. Chem.
, vol.67
, pp. 1738
-
-
Sibi, M.P.1
Liu, P.2
Ji, J.3
Chen, J.4
-
12
-
-
0041315319
-
-
See Supporting Information for the synthesis of 1
-
See Supporting Information for the synthesis of 1.
-
-
-
-
13
-
-
0032538355
-
-
For an excellent recent review, see: Renaud, P.; Gerster, M. Angew. Chem., Int. Ed. 1998, 37, 2562. Also see: Radicals in Organic Synthesis; Renaud, P., Sibi, M. P., Eds.; Wiley-VCH: Weinheim, 2001; Vols. 1 and 2.
-
(1998)
Angew. Chem., Int. Ed.
, vol.37
, pp. 2562
-
-
Renaud, P.1
Gerster, M.2
-
14
-
-
0032538355
-
-
Wiley-VCH: Weinheim
-
For an excellent recent review, see: Renaud, P.; Gerster, M. Angew. Chem., Int. Ed. 1998, 37, 2562. Also see: Radicals in Organic Synthesis; Renaud, P., Sibi, M. P., Eds.; Wiley-VCH: Weinheim, 2001; Vols. 1 and 2.
-
(2001)
Radicals in Organic Synthesis
, vol.1-2
-
-
Renaud, P.1
Sibi, M.P.2
-
15
-
-
0033603905
-
-
(c) Sibi, M. P.; Ji, J.; Sausker J. B.; Jasperse, C. P. J. Am. Chem. Soc. 1999, 121, 7517.
-
(1999)
J. Am. Chem. Soc.
, vol.121
, pp. 7517
-
-
Sibi, M.P.1
Ji, J.2
Sausker, J.B.3
Jasperse, C.P.4
-
16
-
-
0029804421
-
-
(d) Sibi, M. P.; Ji, J.; Wu, J. H.; Gürtler, S.; Porter, N. A. J. Am. Chem. Soc. 1996, 118, 9200.
-
(1996)
J. Am. Chem. Soc.
, vol.118
, pp. 9200
-
-
Sibi, M.P.1
Ji, J.2
Wu, J.H.3
Gürtler, S.4
Porter, N.A.5
-
17
-
-
0042316661
-
-
Varying amounts (1-20%) of the ethyl radical addition/trapping product was also observed depending on the Lewis acid
-
Varying amounts (1-20%) of the ethyl radical addition/trapping product was also observed depending on the Lewis acid.
-
-
-
-
18
-
-
0041315320
-
-
For a discussion on the origins of the high anti selectivity observed in the addition/trapping experiments, see ref 3
-
For a discussion on the origins of the high anti selectivity observed in the addition/trapping experiments, see ref 3.
-
-
-
-
19
-
-
0000457814
-
-
See Supporting Information for details
-
The oxazolidinone functionality in compound 6 was selectively hydrolyzed to a known acid. Pratt, L. M.; Bowles, S. A.; Courtney, S. F.; Hidden, C.; Lewis, C. N.; Martin, F. M.; Todd, R. S. Synlett 1998, 531. See Supporting Information for details.
-
(1998)
Synlett
, pp. 531
-
-
Pratt, L.M.1
Bowles, S.A.2
Courtney, S.F.3
Hidden, C.4
Lewis, C.N.5
Martin, F.M.6
Todd, R.S.7
-
20
-
-
0041315321
-
-
note
-
The amount of ethyl addition byproduct in entries 2-6, Table 2, varied from 1% to 10%. This is an indirect reflection of radical chain length.
-
-
-
-
21
-
-
0042817767
-
-
note
-
The anti stereochemistry for the product was assigned on the basis of analogy.
-
-
-
-
22
-
-
0035801886
-
-
For some selected examples of the synthesis of succinate-based MMP inhibitors, see: (a) Hilpert, H. Tetrahedron 2001, 57, 7675.
-
(2001)
Tetrahedron
, vol.57
, pp. 7675
-
-
Hilpert, H.1
-
23
-
-
0032499266
-
-
(b) Yamamoto, M.; Tsujishita, H.; Hori, N.; Ohishi, Y.; Inoue, S.; Ikeda, S.; Okada, Y. J. Med. Chem. 1998, 41, 1209.
-
(1998)
J. Med. Chem.
, vol.41
, pp. 1209
-
-
Yamamoto, M.1
Tsujishita, H.2
Hori, N.3
Ohishi, Y.4
Inoue, S.5
Ikeda, S.6
Okada, Y.7
-
24
-
-
15444343493
-
-
(c) Levy, D. E.; Lapierre, F.; Liang, W.; Ye, W.; Lange, C. W.; Li, X.; Grobelny, D.; Casabonne, M.; Tyrrell, D.; Holme, K.; Nadzan, A.; Galardy, R. E. J. Med. Chem. 1998, 41, 199.
-
(1998)
J. Med. Chem.
, vol.41
, pp. 199
-
-
Levy, D.E.1
Lapierre, F.2
Liang, W.3
Ye, W.4
Lange, C.W.5
Li, X.6
Grobelny, D.7
Casabonne, M.8
Tyrrell, D.9
Holme, K.10
Nadzan, A.11
Galardy, R.E.12
-
25
-
-
0035952287
-
-
(d) Fray, M. J.; Burslem, M. F.; Dickinson, R. P. Bioorg. Med. Chem. Lett. 2001, 11, 567.
-
(2001)
Bioorg. Med. Chem. Lett.
, vol.11
, pp. 567
-
-
Fray, M.J.1
Burslem, M.F.2
Dickinson, R.P.3
-
28
-
-
0032544135
-
-
(g) Steinman, D. H.; Curtin, M. L.; Garland, R. B.; Davidsen, S. K.; Heyman, H. R.; Holms, J. H.; Albert, D. H.; Magoc, T. J.; Nagy, I. B.; Marcotte, P. A.; Li, J.; Morgan, D. W.; Hutchins, C.; Summers, J. B. Bioorg. Med. Chem. Lett. 1998, 8, 2087.
-
(1998)
Bioorg. Med. Chem. Lett.
, vol.8
, pp. 2087
-
-
Steinman, D.H.1
Curtin, M.L.2
Garland, R.B.3
Davidsen, S.K.4
Heyman, H.R.5
Holms, J.H.6
Albert, D.H.7
Magoc, T.J.8
Nagy, I.B.9
Marcotte, P.A.10
Li, J.11
Morgan, D.W.12
Hutchins, C.13
Summers, J.B.14
-
29
-
-
18344415400
-
-
(h) Pratt, L. M.; Beckett, P.; Bellamy, C. L.; Corkill, D. J.; Cosins, J.; Courtney, P. F.; Davies, S. J.; Davidson, A. H.; Drummond, A. H.; Helfrich, K.; Lewis, C. N. Mangan, M.; Martin, F. M.; Miller, K.; Nayee, P.; Ricketts, M. L.; Thomas, W.; Todd, R. S.; Whittaker, M. Bioorg. Med. Chem. Lett. 1998, 8, 1359.
-
(1998)
Bioorg. Med. Chem. Lett.
, vol.8
, pp. 1359
-
-
Pratt, L.M.1
Beckett, P.2
Bellamy, C.L.3
Corkill, D.J.4
Cosins, J.5
Courtney, P.F.6
Davies, S.J.7
Davidson, A.H.8
Drummond, A.H.9
Helfrich, K.10
Lewis, C.N.11
Mangan, M.12
Martin, F.M.13
Miller, K.14
Nayee, P.15
Ricketts, M.L.16
Thomas, W.17
Todd, R.S.18
Whittaker, M.19
-
30
-
-
0037015438
-
-
Sibi, M. P.; Hasegawa, H.; Ghorpade, S. Org. Lett. 2002, 4, 3343.
-
(2002)
Org. Lett.
, vol.4
, pp. 3343
-
-
Sibi, M.P.1
Hasegawa, H.2
Ghorpade, S.3
-
31
-
-
0042316660
-
-
note
-
2, or TMSONHTMS gave low yields of BB-1101.
-
-
-
|